Synthesis of (+)-casuarine

被引：47

作者：

Denmark, SE ^{[1
]}

Hurd, AR ^{[1
]}

机构：

[1] Univ Illinois, Dept Chem, Roger Adams Lab, Urbana, IL 61801 USA

来源：

ORGANIC LETTERS | 1999年 / 1卷 / 08期

关键词：

D O I：

10.1021/ol9909886

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

[GRAPHICS] The first synthesis of (+)-casiuarine, a pentahydroxy pyrrolizidine alkaloid, is described. The key bond-forming events occur in a tandem [4 + 2]/[3 + 2] nitroalkene cycloaddition involving nitroalkene 6, chiral vinyl ether 7b, and vinyl silane 4. This process also creates five of the six stereocenters present in this potent glycosidase inhibitor. Completion of the synthesis required only four additional steps and delivered (+).casuarine in 20% overall yield.

引用

页码：1311 / 1314

页数：4

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