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
收藏
页码：2962 / 2965
页数：4
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