Stereodivergent Approach to Both C2,8a-syn and C2,8a-anti Relative Stereochemical Manifolds in the Lepadin Family via a TiCl4-Promoted Aza-[3+3] Annulation

被引：9
作者：
Li, Gang
Carlson, Lauren J.
Sagamanova, Irina K.
Slafer, Brian W.
Hsung, Richard P. [1 ]
Gilardi, Claudio
Sklenicka, Heather M.
Sydorenko, Nadiya
机构：
[1] Univ Wisconsin, Div Pharmaceut Sci, Wisconsin Ctr Nat Prod Res, Sch Pharm, Madison, WI 53705 USA
来源：
SYNTHESIS-STUTTGART | 2009年 / 17期
关键词：
titanium(IV) chloride; aza-[3+3] annulation; vinylogous amides; iminium ions; alkaloid synthesis; lepadin alkaloids; stereodivergent approach; episulfide contraction; ENANTIOSELECTIVE TOTAL-SYNTHESIS; VINYLOGOUS AMIDES; CYCLOADDITION REACTIONS; DECAHYDROQUINOLINE ALKALOIDS; EFFICIENT SYNTHESIS; 3+3 ANNELATION; FACILE ENTRY; HYDROGENATION; HETEROCYCLES; DERIVATIVES;
D O I：
10.1055/s-0029-1216920
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Details in developing a stereodivergent approach to the lepadin family and establishing an entry to both C2,8a-syn and C2,8a-anti relative stereochemical manifolds through a common intermediate are described here. This works paves the foundation for constructing all members of the lepadin family, which consists of three subsets based on an array of interesting relative configurations. These efforts underline the prominence of aza-[3+3] annulation as a unified strategy in alkaloid synthesis.
引用
收藏
页码：2905 / 2914
页数：10
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