Synthetic studies towards compounds related to sterpurene and protoilludene

被引：8

作者：

Birkenes, OJ

Hansen, TV

M'dachi, S

Skattebol, L

Stenstrom, Y

机构：

[1] Univ Oslo, Dept Chem, N-0315 Oslo, Norway

[2] Agr Univ Norway, Dept Biotechnol Sci, N-1432 As Nlh, Norway

来源：

ACTA CHEMICA SCANDINAVICA | 1998年 / 52卷 / 06期

关键词：

D O I：

10.3891/acta.chem.scand.52-0806

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

As part of synthetic strategies towards the sesquiterpenes 6-protoilludene and sterpurene the intramolecular aldol condensation of 1-(2-oxopropyl)-2-acetyl-4,4-dimethylcyclopentane was studied in detail. Mixtures of 5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one and 4,8,8-trimethylbicyclo[4.3.0]-3-nonen-2-one were formed. The reaction was carried out under different acidic and basic conditions, giving the two compounds in ratios varying from 1:1 to 12:1. The best conditons were found to be methanesulfonic acid in methanol. The preparation of trans-5,8,8-trimethylbicyclo[4.3.0]-4-nonen-3-one by our route in about 70% overall yield constitutes formally a new synthesis of sterpurene.

引用

页码：806 / 812

页数：7

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