A Hypervalent Iodine-Induced Double Annulation Enables a Concise Synthesis of the Pentacyclic Core Structure of the Cortistatins

被引:98
作者
Frie, Jessica L. [1 ]
Jeffrey, Christopher S. [1 ]
Sorensen, Erik J. [1 ]
机构
[1] Princeton Univ, Dept Chem, Frick Chem Lab, Princeton, NJ 08544 USA
关键词
STEROIDAL ALKALOIDS; ENANTIOSELECTIVE SYNTHESIS; 1,3-DIPOLAR CYCLOADDITION; RING STRUCTURE; ANGIOGENESIS; OXIDATION; REGIOSELECTIVITY; DEAROMATIZATION; ANALOGS;
D O I
10.1021/ol902168g
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A stereocontrolled synthesis of a complex pentacycle embodying the molecular architecture of the cortistatin class of natural products was achieved from the (+)-Hajos-Parrish ketone. The cornerstone of our approach is a hypervalent iodine induced tandem intramolecular oxidative dearomatization and nitrile oxide cycloaddition. The manner in which these ring formations were orchestrated has yielded a rather concise strategy for synthesis.
引用
收藏
页码:5394 / 5397
页数:4
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