Journal
ORGANIC LETTERS
Volume 11, Issue 23, Pages 5394-5397Publisher
AMER CHEMICAL SOC
DOI: 10.1021/ol902168g
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Funding
- National Institute of General Medical Sciences [GM065483]
- Johnson and Johnson
- Merck Research Laboratories for fellowship
- Princeton University Council on Science and Technology
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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.
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