SYNTHESIS OF ALL STEREOISOMERS OF EUDESM-11-EN-4-OL .2. TOTAL SYNTHESIS OF SELIN-11-EN-4-ALPHA-OL, INTERMEDEOL, NEOINTERMEDEOL, AND PARADISIOL - 1ST TOTAL SYNTHESIS OF AMITEOL

被引：35

作者：

KESSELMANS, RPW ^{[1
]}

WIJNBERG, JBPA ^{[1
]}

MINNAARD, AJ ^{[1
]}

WALINGA, RE ^{[1
]}

DEGROOT, A ^{[1
]}

机构：

[1] AGR UNIV WAGENINGEN,ORGAN CHEM LAB,DREYENPLEIN 8,6703 HB WAGENINGEN,NETHERLANDS

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1991年 / 56卷 / 26期

关键词：

D O I：

10.1021/jo00026a012

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The syntheses of (+/-)-selin-11-en-4-alpha-ol (5), (+/-)-intermedeol (6), (+/-)-neointermedeol (7), (+/-)-amiteol (9), and the four remaining unnatural stereoisomers (+/-)-paradisiol (8), (+/-)-7-epi-amiteol (10), (+/-)-5-epi-neointermedeol (11), and (+/-)-5-epi-paradisiol (12) are described. In addition, the related (+/-)-evuncifer ether (25) has been prepared. The syntheses started from the octahydro-8-hydroxy-4a,8-dimethyl-2(1H)-naphthalenones 1-4. The reaction sequence employed for the synthesis of 5, 7, 9, and 12 involved Wittig reaction, oxidative hydroboration, oxidation, equilibration, and olefination. For the synthesis of 6, 8, 10, and 11 the interim equilibration step was omitted. The oxidative hydroboration was the key step in these syntheses.

引用

页码：7237 / 7244

页数：8

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