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A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.

ABSTRACT: 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.

SUBMITTER: Frie JL

PROVIDER: S-EPMC3156445 | biostudies-literature | 2009 Dec

REPOSITORIES: biostudies-literature

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A hypervalent iodine-induced double annulation enables a concise synthesis of the pentacyclic core structure of the cortistatins.

Frie Jessica L JL Jeffrey Christopher S CS Sorensen Erik J EJ

Organic letters 20091201 23

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. ...[more]

PMID: 19943697

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