ENANTIOSELECTIVE TOTAL SYNTHESIS OF BETA-ELEMENE AND FUSCOL BASED ON ENANTIOCONTROLLED IRELAND-CLAISEN REARRANGEMENT

被引：61
|
作者：
COREY, EJ
ROBERTS, BE
DIXON, BR
机构：
[1] Department of Chemistry, Harvard University, Cambridge
来源：
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY | 1995年 / 117卷 / 01期
关键词：
D O I：
10.1021/ja00106a023
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
The potent antiinflammatory agent precursor (+)-fuscol (2) has been synthesized using the chiral reagent 1 to effect the key step, the completely enantioselective Ireland-Claisen rearrangement of ester 3 to acid 4a. Conversion of 4a to the corresponding aldehyde 4c, cation-olefin cyclization to 5a, and deoxygenation produced (+)-beta-elemene (6). (+)-Fuscol (2) was synthesized from 6 via intermediates 7 and 8.
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页码：193 / 196
页数：4
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