SYNTHESIS, BIOTRANSFORMATION AND STEREOCHEMISTRY OF 6-BETA-SESQUITERPENE LACTONES - SYNTHESES OF 6-BETA-ARTEPAULIN, 11,13-DIHYDRO-6-BETA-TUBERIFERIN, 5,15-DIHYDRO-6-BETA-OOPODIN, 4-EPI-6-BETA-VULGARIN AND 6-BETA-VULGARIN

被引：20

作者：

AMATE, Y

BRETON, JL

GARCIAGRANADOS, A

MARTINEZ, A

ONORATO, E

DEBURUAGA, AS

机构：

[1] CSIC,INST PROD NAT ORGAN,LA LAGUNA,SPAIN

[2] UNIV GRANADA,SERV TECN,GRANADA,SPAIN

来源：

TETRAHEDRON | 1990年 / 46卷 / 19期

关键词：

D O I：

10.1016/S0040-4020(01)87881-9

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

6β-Artepaulln, 11,13-dihydro-6Muberiferin, 4,15-dihydro-6α-oopodln, 4-epl--vulgarln and 6β-vutgarin were obtained from a-santonin. Stereochemical studies showed that the configuration at (>6 is decisive In the chemical behaviour of the A ring. Biotransformation of 1 -oxo-5,6aH,4,11 βH-eudesm-2-en-e, 12-olide with Rhaopus nigricans cultures probed to be a very efficient alternative way to obtain 4-epi-6β-vulgarin, which was then converted to G8-vulgarin, a convenient starting material for biogenetical studies of pseudoguaianotides. A new 8β-hydroxyl derivative obtained from this biotransformation constitutes a new approach to the synthesis of 8,12-eudesmanolides and other sesquiterpenolides. Molecular structures were determined mainly by mono- and bidlmensional nmr experiments. © 1990.

引用

页码：6939 / 6950

页数：12

共 36 条

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