Enantiospecific Formal Total Synthesis of (+)-Fawcettimine

被引：60

作者：

Jung, Michael E. ^{[1
]}

Chang, Jonah J. ^{[1
]}

机构：

[1] Univ Calif Los Angeles, Dept Chem & Biochem, Los Angeles, CA 90095 USA

来源：

ORGANIC LETTERS | 2010年 / 12卷 / 13期

基金：

美国国家科学基金会;

关键词：

DONOR-ACCEPTOR CYCLOPROPANES; ORGANIC-SYNTHESIS; CYCLOADDITIONS; PYRROLIDINES; DERIVATIVES; ALDEHYDES; NITRONES;

D O I：

10.1021/ol1009762

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The diastereospecific attack of the silyl end l ether on the activated cyclopropyl diester 27 generated the hydrindanone 28 with complete stereocontrol. Thermal decarbomethoxylation of 28 gave the monoester 29, a key intermediate in Heathcock's synthesis, thereby completing a formal total synthesis of (+)-fawcettimine 1. The analogous cyclization of 33, the diastereomer of 27, afforded the diastereomeric diester 34, thereby demonstrating that the cyclization process is diastereospecific.

引用

页码：2962 / 2965

页数：4

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