The structure of laricinolic acid and its biomimetic transformation into officinalic acid

被引：12

作者：

Erb, B ^{[1
]}

Borschberg, HJ ^{[1
]}

Arigoni, D ^{[1
]}

机构：

[1] ETH Zurich, Organ Chem Lab, CH-8092 Zurich, Switzerland

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2000年 / 15期

关键词：

D O I：

10.1039/b001984o

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Laricinolic acid (8), a new sesquiterpene of the drimane type, has been isolated from the wood-rotting fungus Laricifomes officinalis. Its structure was elucidated by spectroscopic means and confirmed via a correlation with the known drimenine derivative 13. Oxidation of 8 to 1, followed by a mild thermal treatment, furnished (-)-officinalic acid (4) in 65% yield. This transformation establishes the hitherto unknown absolute configuration of the latter. An independent correlation was achieved by pyrolysis of 4 which furnished (-)-dihydrooxoisodrimenine (14) of known absolute configuration.

引用

页码：2307 / 2309

页数：3

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