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Synlett 1996; 1996(12): 1162-1164
DOI: 10.1055/s-1996-5718
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Novel Application of the Intramolecular Prins Reaction: (-)-Anisatin Model Study

Jeffrey A. Charonnat* , Nobuko Nishimura, Bruce W. Travers, Jack R. Waas
  • *Department of Chemistry, California State University, Northridge, 18111 Nordhoff Street, Northridge, CA 91330-8262, USA, Fax (818) 677-2912, E-mail jeff.charonnat@csun.edu
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Publication History

Publication Date:
31 December 2000 (online)

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Hydrolysis of the enol ethers 9a and 9b gave the aldehyde 10 which cyclized in situ to the alcohols 11a and 11b via an intramolecular Prins reaction. Further regio- and stereocontrolled elaboration of the alcohols 11a and 11b afforded the lactone diol 14.

intramolecular Prins - diastereoselective osmylation - (-)-anisatin

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