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Synfacts 2006(3): 0185-0185  
DOI: 10.1055/s-2006-931924
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Isoedunol and β-Araneosene

Contributor(s): Philip Kocienski
J. S. Kingsbury, E. J. Corey*
Harvard University, Cambridge, USA
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Publication History

Publication Date:
21 February 2006 (online)

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Significance

The syntheses of Isoedunol and β-Araneosene feature a 3 → 4 pinacol ring expansion, a simultaneous 4 → 5 pinacol ring expansion/12 → 11 ring contraction and a SmI2-mediated pinacol coupling to construct a 12-membered ring. The α-hydroxy ester derivative A is the most hindered substrate successfully used in a Kulin­kovich reaction to date.