Synthesis of psudoheliotridane via formal [3+2] annulation and ring-closing metathesis

被引：16

作者：

Chang, MY

Hsu, RT

Tseng, TW

Sun, PP

Chang, NC

机构：

[1] Natl Univ Kaohsiung, Dept Appl Chem, Kaohsiung 811, Taiwan

[2] Natl Sun Yat Sen Univ, Dept Chem, Kaohsiung 804, Taiwan

来源：

TETRAHEDRON | 2004年 / 60卷 / 26期

关键词：

stepwise [3+2] annulation; ring-closing metathesis; psudoheliotridane;

D O I：

10.1016/j.tet.2004.04.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Base-induced coupling/cyclization stepwise [3+2] annulation of alpha-sulfonylacetamide with (Z)-2-bromoacrylates yielded polysubstituted pyroglutamates with three contiguous chiral centers with trans-trans orientation in a one-pot synthesis. The pyrrolizidine skeleton was obtained via the ring-closing metathesis (RCM) method. This facile strategy was used to synthesize psudoheliotridane. (C) 2004 Elsevier Ltd. All rights reserved.

引用

页码：5545 / 5550

页数：6

共 45 条

[1] SATURATED PYRROLIZIDINEDIOLS .2. TOTAL SYNTHESIS AND STEREOCHEMISTRY OF MACRONECINE [J].