Flexible Approach to Stemona Alkaloids: Total Syntheses of (-)-Stemospironine and Three New Diastereoisomeric Analogs

被引：15
作者：
Bardaji, Nuria [1 ]
Sanchez-Izquierdo, Francisco [1 ]
Alibes, Ramon [1 ]
Font, Josep [1 ]
Busque, Felix [1 ]
Figueredo, Marta [1 ]
机构：
[1] Univ Autonoma Barcelona, Dept Quim, Bellaterra 08193, Spain
来源：
ORGANIC LETTERS | 2012年 / 14卷 / 18期
关键词：
EFFICIENT SYNTHESIS; OXIDATION; ALCOHOLS;
D O I：
10.1021/ol302185j
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Total syntheses of (-)-stemospironine and three new diastereoisomeric analogs have been completed through a flexible strategy devised for Stemona alkaloids. The azabicycle 7 is the pivotal intermediate, from which the sequence splits according to each particular target. The most remarkable differential feature for stemospironine is the installation of the spiranic gamma-lactone through an intramolecular Horner-Wadsworth-Emmons olefination. The configuration of the stereogenic center at C-11 was controlled by fine-tuning of the synthetic sequence.
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收藏
页码：4854 / 4857
页数：4
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