JPS5953271B2 - Sesquiterpene derivatives and their production method - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a novel sesquiterpene derivative and a method for producing the same.

The compound of the present invention has the general formula (wherein R1 and R2 together represent a lower lalene dioxy group).

) is a sesquiterpene derivative represented by the compound.

All of the compounds of the present invention are novel compounds that have not been described in any literature and have the physical properties described in the Examples below.

The compound of the present invention is a known substance barburganal (War
Barbaganal is an important intermediate in the total synthesis of Barbaganal, and the final synthetic substance, Barbaganal, is a natural product derived from the East African plant Barburgia.
urgia), its structural formula has also been determined, and its physiological activity is similar to that of the night robber moth (Armyw).
A powerful antifeedant (Antifee) against
dant) [Chem. COmm. p. (1976)]. The compound of the present invention is useful as an important intermediate in the next step in the total synthesis of barbarganal.

In the above step, the starting material 7-oxoisodrimenin (7-oxoisodrimenin) is isolated as a natural product, isodorimenine (IsOdrimenin).
drimenine) [J. Chem. SOc. ,p●
4685 (1960)] with an oxidizing agent, especially chromic acid [H. Ap
peI, etal: J. C. S, 4685 (1960)
], and the raw material isodorimenine was prepared by the present inventor,
Total synthesis has already been achieved as a sesquiterpene derivative derived from l-abietic acid, and it is easily available [Japanese Patent Application No. 52-38,628 (Japanese Unexamined Patent Publication No. 53-1
24,256)].

Furthermore, the present inventors have also succeeded in synthesizing isodorimenine from easily available β-ionone (β-10n0ne) in an extremely short process (Japanese Patent Publication No. 6313/1983). To explain the above steps, the starting material 7-oxoisodorimenine is first induced into a ketal form, then a ketone form, diacetate form, epoxy form, triol form, silyl form; Garpone: lower form, dialcohol form, aldehyde form, Barbaganal can be synthesized by converting it into a ketal, diol, and aldehyde, respectively. To explain this step by step, first, starting material 7
- By treating oxoisodorimenine (2) with a dialcohol and an organic acid and refluxing it, the ketal compound (3) can be obtained in high yield.

The obtained ketal body (3) can be reacted with a reducing reagent in an organic solvent to lead to the ketone body (4) in high yield.

By reacting the obtained ketone body (4) with an acetylating agent in a solvent, the diacetate body (5) can be obtained in high yield.

The epoxy compound (6) is obtained in high yield by treating the obtained diacetate compound (5) with a peroxide in the presence of an aqueous alkali solution.

The obtained epoxy body (6) is reacted with hydrazine hydrate to introduce a double bond to obtain a triol body (7).

The obtained triol body (7) can be reacted with imidazole and trialkylsilyl chloride to obtain a silyl body (8) in which the hydroxyl group of the aryl group is protected.

The obtained silyl compound (8) is refluxed with phosgene or carbonylimidazole to obtain a carbonate compound (9) in which glycol is protected with carbonate in a high yield.

By treating the obtained carbonate form (9) with an organic acid, the silyl is returned to alcohol, and the alcohol form (9) is converted into an alcohol form.
) can be obtained quantitatively.

When the obtained alcohol is reacted with an oxidizing agent, aldehyde αυ can be obtained in high yield.

The obtained aldehyde αυ is further treated with a dialcohol and an organic acid to protect it with an acetal, thereby obtaining alkali-stable ketal 03.

By treating the obtained ketal form ◎ with an alkali, a diol form, the compound of the present invention (self), can be obtained in high yield.

The obtained diol compound 1 is reacted with an oxidizing agent under basic or neutral conditions to obtain an aldehyde compound (auto).

When the thus obtained aldehyde (auto) is reacted with an organic acid, the above-mentioned barburganal (auto) is obtained. Barberganal (auto) synthesized in this way completely matches the physical properties of the natural product Barberganal.
The compound of the present invention can be produced by the following method.

That is, the ketal compound (3) can be obtained in high yield by treating the 7-oxoisodorimenine (2) with a dialcohol and an organic acid and refluxing it.

In this case, organic acids such as p-toluenesulfonic acid and Ganfersulfonic acid are used, aromatic hydrocarbons such as benzene and toluene are used as solvents, and ethylene glycol, 1,3 -Probanediol etc. can be used, especially in benzene solution, p
- It is preferable to use toluenesulfonic acid or ethylene glycol.

The reaction temperature and reaction time at this time are not particularly limited, but
80-150°C and 4-12 hours are suitable, respectively.

The obtained ketal body (3) can be reacted with a reducing reagent in an organic solvent to lead to the ketone body (4) in high yield.

In the above reaction, lithium aluminum hydride is suitably used as the reducing reagent, and ethers such as ether, dioxane, and tetrahydrofuran are used as the solvent. In particular, when lithium aluminum hydride is used in anhydrous ether, suitable.

The reaction temperature and reaction time are not particularly limited, and room temperature and 2 to 12 hours are suitable, respectively.

By reacting the obtained ketone body (4) with an acetylating agent in a solvent, diacetate monomer (5) can be obtained in high yield. As the acetylating agent in this case, acetic anhydride-pyridine, acetyl-pyridine chloride, etc. can be used, but particularly excellent results are obtained in the case of acetic anhydride monopyridine. In the above reaction, the reaction temperature and reaction time are not particularly limited, and particularly suitable results are obtained at room temperature for 4 to 12 hours.

The epoxy compound (6) is obtained in high yield by treating the obtained diacetate compound (5) with a peroxide in the presence of an aqueous alkali solution.

The alkali used in this case is an aqueous solution of sodium hydroxide, potassium hydroxide, etc., the peroxide used is hydrogen peroxide, t-butyl hydroperoxide, etc., and the solvent is alcohol, ester, etc. Hydrogen peroxide in methanol solvent in the presence of sodium hydroxide is particularly preferred.

Although the reaction temperature and reaction time are not particularly limited, a temperature around 0° C. and a time of 1 to 4 hours is suitable.

The obtained epoxy body (6) is reacted with hydrazine hydrate to introduce a double bond to obtain a triol body (7).

As the hydrazine, 100% hydrazine hydrate is suitable, and a solvent is not particularly required, and the reaction proceeds advantageously even in the absence of a solvent.

Reaction temperature and reaction time are not particularly limited, but 120°C
Around 10 to 30 minutes (room temperature is also acceptable) and 10 to 30 minutes are suitable.

The obtained triol body (7) can be reacted with imidazole and trialkylsilyl chloride to obtain a silyl body (8) in which the hydroxyl group of the aryl group is protected.

In this reaction, dimethyl t-butylsilyl chloride gives suitable results as the trialkylsilyl chloride.

Solvents include DMF (dimethylformamide), DMSO (
Organic solvents such as dimethyl sulfoxide) and acetate can be used as appropriate, and DMF is particularly suitable.

The reaction temperature and reaction time are not particularly limited, but especially -1
00-0°C and 10-60 minutes are preferred.

Further, the obtained silyl compound (8) is refluxed with phosgene or carbonyl isidazole to obtain a carbonate compound (9) in which the carbonate is protected with glycol in a high yield.

In this reaction, phosgene can be used, but N,N'-carbonylimidazole is preferably used because it is a dangerous gaseous substance. As the solvent, organic solvents such as benzene and chloroform are used. In addition, the reaction temperature and reaction time are not particularly limited, but especially around 90°C and 30 to 30°C.
60 minutes is preferred. By treating the obtained carbonate compound 9 with an organic acid, the silyl is returned to alcohol, and the alcohol compound (substitute) is obtained in a quantitative ratio.

Organic acids used in this reaction include Ganfer sulfonic acid, p-toluenesulfonic acid, trifluoroacetic acid, acetic acid, etc. Alcohols, ethers, etc. can be used as solvents, especially in methanol. It is preferable to use ganfer sulfonic acid.

The reaction temperature and reaction time at this time are not particularly limited, but
Particularly good results are obtained at room temperature for 3 to 5 hours.

When the obtained alcohol α0 is reacted with an oxidizing agent, aldehyde συ is obtained in high yield.

The oxidant used in this oxidation reaction is John's (JO
nes) reagent (chromic anhydride in dilute sulfuric acid) is preferably used, and acetone is particularly effectively used as the solution.The reaction temperature and reaction time are not particularly limited, but each -
The reaction proceeds at 10° C. to 0° C. and in a short period of about 5 to 30 minutes.

The obtained aldehyde αυ is further treated with a dialcohol and an organic acid in order to protect it with an acetal, thereby obtaining an alkali-stable ketal l.

In this case, organic acids such as p-toluenesulfonic acid and Ganfersulfonic acid are used, and aromatic hydrocarbons such as benzene and toluene are used as the solvent.
Dialcohols include ethylene glycol, 1,3-
Propanediol and the like can be used, and p-toluenesulfonic acid and 1,3-propanediol in a benzene solution are particularly preferred.

The reaction temperature and reaction time at this time are not particularly limited, but
Each reacts well at 80 to 150°C and in a short time of about 10 to 30 minutes.

By treating the obtained ketal compound I with an alkali, the compound of the present invention, the diol compound (auto), can be obtained in high yield.

As the alkali in this case, an aqueous solution such as sodium hydroxide or potassium hydroxide can be used, and as the solvent, ethers such as ether, dioxane, and tetrahydrofuran can be used, but in particular, it is preferable to use sodium hydroxide in the dioxane solution. suitable.

The reaction temperature and reaction time are not particularly limited, but at room temperature
~3 hours is preferred. EXAMPLES Below, the method for producing the compound of the present invention will be specifically explained with reference to Examples.

Reference Example 1 Chromic acid 400W9 is added to 30d of an acetic acid solution of 318η of Taichi isodomenine (1) and stirred at 50°C for 4 hours.

After the reaction, water was added and extracted with ether, and the ether layer was extracted with water and
After washing with saturated sodium bicarbonate water and saturated saline, dry with sodium chloride. Then, when the solvent was distilled off, an oily substance 30111
f is obtained.

This was subjected to silica gel column chromatography (LOba
rcOlumn:hexane:acetic ether=3:1) to obtain 7-oxoisodorimenine (2) 239W1f. This is further recrystallized from n-hexane-ether to obtain colorless prism crystals. 7-oxoisodorimenine (2) obtained in Reference Example 1 254'! Add 2d of ethylene glycol and 30Tn of p-toluenesulfonic acid to 20WLe of a benzene solution of No. 19 to prepare Dean-Starck (D
ean-Stark apparatus overnight. After the reaction,
The benzene layer was washed with 10% aqueous sodium carbonate and saturated brine, and then dried over magnesium sulfate. After distilling off the solvent, silica gel column chromatography (LObarcOlum
n:hexane:acetic ether=3:1) to obtain ketal compound (3) 2817!1f. When this is further recrystallized from n-hexane-ether, colorless prism crystals are obtained.

(Physical Properties) Example 2 Lithium aluminum hydride 29 d was added to 100 d of anhydrous ether solution of ketal compound (3) 3.39 obtained in Example S1.
and stirred at room temperature for 2 hours and 30 minutes.

After the reaction, water and 10% HCI are added, followed by ether extraction, and the ether layer is washed with saturated brine and dried over magnesium sulfate. When the solvent is distilled off, the ketone body (4) 2.9609
is obtained. (Physical properties) Mass spectrometry: WVe: 234 (M+-H, O
) (high resolution mass spectrum) 1R (CCj4):Vm
ax34OO, l665CllL-1▲●crystal v\↓▼▲
ν Example 3 / Anhydrous vinegar IlOmI to a pyridine solution of 2.960 g of the ketone body (4) obtained in Example 2 107!11. Add and leave at room temperature for 4 hours.

Against? Thereafter, water is added under cooling and extracted with ether, and the ether layer is washed with 10% HCII, 10% Na2cO3, and saturated brine, and then dried over magnesium sulfate. After distilling off the solvent,
Silica gel chromatography (hexane ether)
1:1), diacetate body (5) 2.550f!
get. When this is further recrystallized from n-hexane-ether, colorless needle crystals are obtained. (Physical properties) Example Diacetate compound (5) obtained in Example 3 1.0609
Add 5 d of 30% hydrogen peroxide, then 2.5 d of 10 Ifb sodium hydroxide to a methanol solution of 3011, and heat at 0°C.
Stir for 1 hour.

After the reaction, the bath medium was distilled off and extracted with ether. The ether layer was washed with saturated brine and dried over magnesium sulfate. When the solvent is distilled off, 835 crystals of epoxy compound (6) are obtained.
When this is further recrystallized from ether-hexane, colorless needle-shaped crystals are obtained. (Physical properties) Melting point: 117-118°C Elemental analysis value: Calculated value C: 67.13H: 9.02 Actual value C: 67.11H: 9.08lR (CHC2,): Vm
ax 3590, 3460, 1695cm-1NMR (
CDC23): δO. 84 (Me) 0.86 (Me) 1
．． 13(Me) Example 5 Eboxy body (6) obtained in Example 4 100 to 835 w
Add %NH, NH2・H, O12d and heat at 120℃ for 15
Heat for a minute.

After the reaction, the mixture is extracted with ether, and the ether layer is washed with saturated brine and dried over magnesium sulfate. When the solvent is distilled off,
Triol form (7) 720 mI! is obtained. Partially preparative thin layer chromatography (silica gel: ethyl acetate)
When recrystallized from ether, it becomes colorless prismatic crystals. (Physical properties) Melting point: 137-138
℃ Mass:αre'e:223(M+-CH,OH
)lR(CHCI goose)! max 3470d-1NMT
L (CDCis): 0.80 (Me) 0.90 (Me)
0.92(Me) 5.86(broad, 7→D Example 6 Triol body (7) obtained in Example 5 106111f
Dimethylformamide solution of 21! Imidazole 857!9 is added to the mixture, followed by 1 d of a dimethylformamide solution of dimethyl t-butylsilyl chloride 63119, and the mixture is stirred for 20 minutes under ice cooling.

After the reaction, the mixture is extracted with ether, and the ether layer is washed with saturated brine and dried over magnesium sulfate. After evaporation of the solvent, preparative thin layer chromatography (silica gel: hexane: ether = 1:1) was performed to obtain 841!L of the silyl compound (8).
get f. (Physical properties) Mass: rrVe: 337 (M+-CH20H
)lR(CHCl3):Vmax 3420clL-1
NMR (CDCI, ): 5.81 (broad: 7-H
) Example 7 Silyl compound (8) obtained in Example 6 194
342 η of N,N'-carbonyldiimidazole was added to 15 WLt of a benzene solution of η and refluxed for 30 minutes.

Next, ether was added, washed with saturated saline, and dried over magnesium sulfate. When the solvent is distilled off, 224 mf of carbonate {9) is obtained. When recrystallized from n-hexane, fine colorless needle crystals are obtained. (Physical properties) Melting point: 59-6'C Elemental analysis value: (calculated value) C, 66.96l-L9.7l
(Actual measurement value) C, 67.26H, 9.73lR (CHCl
3) :νMaxl785C! RL″1NMR (CDC
l3): 4.17 (S; -CH2-0S1) Example 15 mg of Ganfer sulfonic acid was added to 6 ml of a methanol solution of 63η of the carbonate compound (9) obtained in Example 7,
Stir at room temperature for 3 hours.

After the reaction, the solvent is distilled off, the mixture is extracted with ether methylene chloride, and the ether monochloride solution is washed with saturated aqueous sodium bicarbonate and saturated brine, and then dried over magnesium sulfate.
After distilling off the solvent, it is crystallized with n-hexane-ether to obtain alcohol QO) 45119.

Recrystallization from n-hexane-benzene gives colorless needle-like crystals. (Physical properties) Melting point: 146-149℃ Elemental analysis value: (calculated value) C, 68.54H, 8.63 (
Actual measurement value) C, 68.98H, 8.8OlR (CHCl3
): Vmax36OO, 34OO, l7855L-1N
MR (CDCl3): 0.82 (Me) 0.90 (Me
) 0.92 (Me) 4.19 (S; 2H, C, -0H) Example 6 drops of JOnes reagent were added to 6d of the acetone solution of the alcohol AI69W9 obtained in Example 8 under ice-cooling and stirring. After adding, stir for 5 minutes.

After the reaction, isoprobanol was added, the solvent was distilled off, water was added, ether monochloride was extracted, the ether monochloride solution was washed with saturated brine, saturated sodium bicarbonate, and saturated brine, and then magnesium sulfate was added. Dry with.
When the solvent is distilled off, aldehyde a1) 69W is obtained. When recrystallized from benzene-n-hexane, colorless needle-like crystals are obtained. (Physical properties) Melting point: 133-135 color C Elemental analysis value: (calculated value) C, 69. O4l-L7.97
(Actual measurement value) C, 68.97ll, 8. l3lR(CHC
l3): νMaxl79O, l695C7n-1NMR
(CDCl3): δ0.83(Me) 0.94(Me) 0.96(Me) Example 10 1.5 d of 1,3-propanediol was added to 40 d of the benzene solution of the aldehyde AD3Ogllf obtained in Example 9.
and a small amount of p-toluenesulfonic acid and refluxed for 15 minutes in a Dean-Stark apparatus.

After the reaction, ether is added and the ether layer is washed with 1C% sodium carbonate solution and saturated brine, and then dried over magnesium sulfate. After evaporation of the solvent, crystallization is performed with ether-hexane to obtain a ketal compound 0213601V. Recrystallization from ether-hexane gives colorless needle-shaped crystals.

(Physical properties) Melting point: 167-168℃ Elemental analysis value: (calculated value) C, 67.83″H. 8.39
(Actual value) A67.92H. 8.42 lR(CHCl3): Vmaxl78OCI! L-1N
MR(CDCll3): δ0.80(Me)0.88(
Me) 0.91(Me) 4.30(D, J=9;Cdan,{)C{))5.04(
S;a)) 5.12(D,Je9;CI{!-{)C-0)6.3
1 (D, d, J = 5, 2; 7 → 0 Example 11 To 10 d of the dioxane solution of the ketal A32OOOW9 obtained in Example 10, 3 d of 10% sodium hydroxide solution and 51 t of water were added for 1 hour and 30 minutes. , stir at room temperature.

After the reaction, the mixture is extracted with ether, and the ether layer is washed with saturated brine and then dried over magnesium sulfate. After distilling off the solvent,
The mixture was subjected to silica gel chromatography (hexane ether = 1:4) to obtain diol compound 03181mf.

Recrystallization from ether-hexane gives colorless columnar crystals. (Physical properties) Melting point: 99-100℃ Elemental analysis value: (calculated value) C, 69.64H, 9.74 (
Actual measurement value) C, 69.77l-L9.75lR (CHCi
3): Vmax35OOCIIL-1NMR (CDCl
3):0.87(Me) 0.91(2×Me) 5.14(S;3Δ) 6.23(BrOad,7−}IY

Claims (1)

[Claims] 1. A compound represented by the general formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ (However, in the formula, R_1 and R_2 together represent a lower alkylenedioxy group.) 2 React the compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ with hydrazine hydrate to obtain the compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. React with alkylsilyl chloride to obtain a compound represented by the formula ▲Mathematical formulas, chemical formulas, tables, etc.▼, and further react with phosgene or carbonyldiimidazole to obtain the compound represented by the formula Process of obtaining a compound represented by the formula ▲ Mathematical formula, chemical formula, table, etc. by treating this with an organic acid Process of obtaining a compound represented by the formula ▲ Mathematical formula, chemical formula, table, etc. There is a process of obtaining a compound represented by ▼, which is treated with a dialcohol and an organic acid, and has the formula ▲mathematical formula, chemical formula, table, etc.▼ (However, in the formula, R_1 and R_2 together form a lower alkylenedioxy group. There are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼, which are characterized by the process of obtaining a compound represented by A method for producing a compound represented by (representing a lower alkylenedioxy group). 3 By treating the compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ with peroxide in the presence of an alkaline solution, the compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ is obtained. This is reacted with hydrazine hydrate to obtain a compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ This is further reacted with imidazole and trialkylsilyl chloride to obtain the compound represented by the formula ▲ Numerical formulas, chemical formulas, tables, etc. There is a process of obtaining a compound represented by ▼ and further reacting it with phosgene or carbonyldiimidazole to obtain a compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▲There are mathematical formulas, chemical formulas, tables, etc.▼ The process of obtaining a compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ The process of obtaining a compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. The process of obtaining a compound represented by the formula ▲numerical formula, chemical formula, table, etc.▼ (in the formula, R_1 and R_2 together represent a lower alkylenedioxy group) by treatment with an acid, and this is treated with an alkali. There is a method for producing a compound represented by the general formula ▲ mathematical formula, chemical formula, table, etc. ▼ (wherein R_1 and R_2 together represent a lower alkylene dioxy group), which is characterized by going through the steps of . 4 A compound represented by the formula ▲ includes mathematical formulas, chemical formulas, tables, etc. ▼ is reacted with an acetylating agent to form the formula ▲
There are mathematical formulas, chemical formulas, tables, etc. By obtaining a compound represented by ▼ and treating this compound with peroxide in the presence of an alkaline solution, the formula ▲ mathematical formula,
A compound represented by the formula ▼ is obtained, and this is reacted with hydrazine hydrate to obtain a compound represented by the formula ▲, which is further combined with imidazole and trialkylsilyl. React with chloride to obtain a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and further react with phosgene or carbonyldiimidazole to obtain a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ The process of obtaining a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ by treating this with an organic acid.The process of obtaining a compound represented by the formula ▲There are formulas, chemical formulas, tables, etc.▼ The process of obtaining a compound represented by the formula ▲mathematical formula, chemical formula, table, etc.▼ (wherein R_1 and R_2 together represent a lower alkylene dioxy group) by treating this with a dialcohol and an organic acid. There are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼, which are characterized by the process of obtaining a compound represented by A method for producing a compound represented by (representing a dioxy group). 5 React the compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ with lithium aluminum hydride to obtain the compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ and use this compound as an acetylating agent. By reacting with, a compound represented by the formula ▲ has a mathematical formula, chemical formula, table, etc. ▼, and by treating this compound with peroxide in the presence of an alkaline solution, the formula ▲
A compound represented by the formula ▼ is obtained, and this is reacted with hydrazine hydrate to obtain a compound represented by the formula ▲, which is further combined with imidazole and trialkylsilyl. React with chloride to obtain a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and further react with phosgene or carbonyldiimidazole to obtain a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ The process of obtaining a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ by treating this with an organic acid.The process of obtaining a compound represented by the formula ▲There are formulas, chemical formulas, tables, etc.▼ The process of obtaining a compound represented by the formula ▲mathematical formula, chemical formula, table, etc.▼ (wherein R_1 and R_2 together represent a lower alkylene dioxy group) by treating this with a dialcohol and an organic acid. There are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼, which are characterized by the process of obtaining a compound represented by A method for producing a compound represented by (representing a dioxy group). 6 A compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc.▼ is reacted with a dialcohol and an organic acid to obtain a compound represented by the formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼, and this compound is hydrogenated. React with lithium aluminum to obtain a compound represented by the formula ▲Mathematical formula, chemical formula, table, etc.▼, and react with an acetylating agent to obtain a compound represented by the formula ▲Mathematical formula, chemical formula, table, etc.▼ By obtaining a compound and treating this compound with peroxide in the presence of an alkaline solution, the formula ▲
A compound represented by the formula ▼ is obtained, and this is reacted with hydrazine hydrate to obtain a compound represented by the formula ▲, which is further combined with imidazole and trialkylsilyl. React with chloride to obtain a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼, and further react with phosgene or carbonyldiimidazole to obtain a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ The process of obtaining a compound represented by the formula ▲There are mathematical formulas, chemical formulas, tables, etc.▼ by treating this with an organic acid.The process of obtaining a compound represented by the formula ▲There are formulas, chemical formulas, tables, etc.▼ The process of obtaining a compound represented by the formula ▲mathematical formula, chemical formula, table, etc.▼ (wherein R_1 and R_2 together represent a lower alkylene dioxy group) by treating this with a dialcohol and an organic acid. There are general formulas ▲mathematical formulas, chemical formulas, tables, etc.▼, which are characterized by the process of obtaining a compound represented by A method for producing a compound represented by (representing a dioxy group).