A Hypervalent Iodine-Induced Double Annulation Enables a Concise Synthesis of the Pentacyclic Core Structure of the Cortistatins
- 30 October 2009
- journal article
- letter
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 11 (23), 5394-5397
- https://doi.org/10.1021/ol902168g
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.Keywords
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