First asymmetric total synthesis of (-)-(R)- and (+)-(S)-geibalansine

被引：16
|
作者：
Morel, AF [1 ]
Larghi, EL [1 ]
机构：
[1] Univ Fed Santa Maria, Lab 2122B, BR-97119900 Santa Maria, RS, Brazil
来源：
TETRAHEDRON-ASYMMETRY | 2004年 / 15卷 / 01期
关键词：
D O I：
10.1016/j.tetasy.2003.09.052
中图分类号：
O61 [无机化学];
学科分类号：
070301 ; 081704 ;
摘要：
Treatment of prochiral chromenoquinoline 2 with (R,R)- and (S, S)-(1,4-di-tert-butyl-salicilydene)-diaininocycloilexane (manganese 111) chloride, and buffered house bleach (pH - 11) gave the epoxide 3 with 90-95% yield and ee >93% (estimated by polarimetry). The epoxides were opened with H-2 Pd/C 10% affording geibalansine 1 in 75% yield and ee 94-98%, determined by HPLC analysis. (C) 2003 Elsevier Ltd. All rights reserved.
引用
收藏
页码：9 / 10
页数：2
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