Total synthesis of (+)-β-himachalene

被引:10
|
作者
Ho, TL [1 ]
Chein, RJ [1 ]
机构
[1] Natl Chiao Tung Univ, Dept Appl Chem, Hsinchu, Taiwan
关键词
D O I
10.1002/hlca.200690025
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
An enantioselective synthesis of (+)-beta-himachalene (2) was accomplished starting from (1S,2R)-1,2-epoxy-p-menth-8-ene (3) in 15 or 16 steps with an overall yield of ca. 6% (Schemes 3, 5, and 6). Key transformations include an Ireland Claisen rearrangement, a Corey oxidative cyclization, and a ring expansion.
引用
收藏
页码:231 / 239
页数:9
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