Total synthesis of (+)-epiepoformin, (+)-epiepoxydon and (+)-bromoxone employing a useful chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclohexanecarboxylate

被引：50
|
作者：
Tachihara, T
Kitahara, T
机构：
[1] Univ Tokyo, Grad Sch Agr & Life Sci, Dept Appl Biol Chem, Bunkyo Ku, Tokyo 1138657, Japan
[2] T Hasegawa Co Ltd, Tech Res Ctr, Nakahara Ku, Kawasaki, Kanagawa 2110022, Japan
来源：
TETRAHEDRON | 2003年 / 59卷 / 10期
关键词：
total synthesis; natural epoxycyclohexene derivatives; chiral building block;
D O I：
10.1016/S0040-4020(03)00119-4
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Enantioselective total synthesis of (+)-epiepofortnin 1, (+)-epiepoxydon 2 and (+)-bromoxone 3 using a chiral building block, ethyl (1R,2S)-5,5-ethylenedioxy-2-hydroxycyclo- hexanecarboxylate 6, is described. Since the synthesis afforded intermediates 18, 2 and 25, it accomplished a formal synthesis of (-)-theobroxide 19, (-)-phyllostine 22, (+)-herveynone 27 and (-)-asperpentyn 28. The usefulness of 6 for the synthesis of natural epoxycyclohexene derivatives was demonstrated. (C) 2003 Elsevier Science Ltd. All rights reserved.
引用
收藏
页码：1773 / 1780
页数：8
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