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.

引用

页码：193 / 196

页数：4

共 21 条

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