Synthetic application of acylnitroso Diels-Alder derived aminocyclopentenols: Total synthesis of (+)-streptazolin

被引：29
|
作者：
Li, FZ [1 ]
Warshakoon, NC [1 ]
Miller, MJ [1 ]
机构：
[1] Univ Notre Dame, Dept Chem & Biochem, Notre Dame, IN 46556 USA
来源：
JOURNAL OF ORGANIC CHEMISTRY | 2004年 / 69卷 / 25期
关键词：
D O I：
10.1021/jo048606j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Concise total syntheses of (+)-streptazolin 1 and its more stable dihydro derivative 2 were accomplished via an intramolecular aldol condensation strategy starting from readily available aminocyclopentenol (-)-7. The synthetic sequence included reductive amination, stereoselective epoxidation, intramolecular aldol (and condensation) reaction, and Wittig reaction. The overall yield for dihydro derivative 2 from aminocyclopentenol (-)-7 was about 7% for a total of 14 steps.
引用
收藏
页码：8836 / 8841
页数：6
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