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Enantioselective Total Synthesis of Isoedunol and β-Araneosene Featuring Unconventional Strategy and Methodology

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Jason S. Kingsbury and E. J. Corey*

Department of Chemistry and Chemical Biology, Harvard University, Cambridge, Massachusetts 02138

J. Am. Chem. Soc., 2005, 127 (40), pp 13813–13815

DOI: 10.1021/ja055137+

Publication Date (Web): September 15, 2005

In papers with more than one author, the asterisk indicates the name of the author to whom inquiries about the paper should be addressed.

, corey@chemistry.harvard.edu

Abstract

A new synthetic strategy for the enantioselective synthesis of members of the dolabellane family of marine natural products has been demonstrated for the specific examples β-araneosene and isoedunol (1 and 2, respectively) by the pathway outlined in Scheme 1. Key steps include (1) diastereoselective alkylation of Seebach's chiral lactate acetal (6) by the iodide derived from 5; (2) Kulinkovich ethylenation of ester 9 to form the cyclopropanol 10; (3) ring expansion of 10 to form 11; (4) pinacol cyclization of keto aldehyde 12 to form 13a; (5) rearrangement of 13b to 14; (6) propenylation of 14 to 2; and (7) reductive π-transposition to form 1.

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History

Published In Issue October 12, 2005
Received July 28, 2005

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Communication

Enantioselective Total Synthesis of Isoedunol and β-Araneosene Featuring Unconventional Strategy and Methodology