SYNTHETIC STUDIES OF SESQUITERPENES WITH A CIS-FUSED DECALIN SYSTEM .4. SYNTHESIS OF (+)-5-BETA-H-EUDESMA-3,11-DIENE, (-)-5-BETA-H-EUDESMANE-4-BETA,11-DIOL AND (+)-5-BETA-H-EUDESMANE-4-ALPHA,11-DIOL, AND STRUCTURE REVISION OF A NATURAL EUDESMANE-4,11-DIOL ISOLATED FROM PLUCHEA-ARGUTA
SYNTHETIC STUDIES OF SESQUITERPENES WITH A CIS-FUSED DECALIN SYSTEM .4. SYNTHESIS OF (+)-5-BETA-H-EUDESMA-3,11-DIENE, (-)-5-BETA-H-EUDESMANE-4-BETA,11-DIOL AND (+)-5-BETA-H-EUDESMANE-4-ALPHA,11-DIOL, AND STRUCTURE REVISION OF A NATURAL EUDESMANE-4,11-DIOL ISOLATED FROM PLUCHEA-ARGUTA
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DOI：
10.1021/np50111a001
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发表时间：
1994-09-01
影响因子：
5.1
通讯作者：
ISOGAI, K
中科院分区：
文献类型：
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作者：
ANDO, M;ARAI, K;ISOGAI, K
以cr-santonin为起始原料，通过明确的方法合成了（+）-5 β H-桉烷-3，11-二烯[1]、（-）-5 β H-桉烷-4 β，11-二醇[2]和（+）-5 β H-桉烷-4 α，11-二醇[15]。二烯1与先前作为白蚁防御物质分离的天然产物相同。尽管最近提出了从Pluchea plutta中分离的一种新的桉烷-1，4-二醇[A]的结构2，但当比较它们的物理和光谱参数时，合成的2及其C-4差向异构体15与这种天然桉烷-4，11-二醇并不相同。这种天然桉烷-4，11-二醇的结构已从2修改为3（7 β H-桉烷-4 α，11-二醇），作为相关天然和非天然桉烷衍生物的H-1-和C-13-NMR光谱分析的结果。
The syntheses of (+)-5 beta H-eudesma-3,11-diene [1], (-)-5 beta H-eudesman- 4 beta,11-diol [2], and (+)-5 beta H-eudesmane-4 alpha,11-diol [15] were carried out by an unambiguous procedure starting from cr-santonin. The diene 1 was identical with a natural product which was isolated previously as a termite defense substance. Although structure 2 was recently proposed for a new eudesmane-1,4-diol [A] isolated from Pluchea arguta, synthetic 2 and its C-4 epimer, 15, were not identical with this natural eudesmane-4,11-diol when their physical and spectroscopic parameters were compared. The structure of this natural eudesmane-4,11-diol has been revised from 2 to 3 (7 beta H-eudesmane-4 alpha,11-diol) as a result of the analysis of the H-1- and C-13-nmr spectra of related natural and unnatural eudesmane derivatives.