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

来源：

ORGANIC LETTERS | 2009年 / 11卷 / 23期

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

页码：5394 / 5397

页数：4

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