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Synlett 1996; 1996(1): 31-33
DOI: 10.1055/s-1996-5327
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A Biogenetic Approach to Halicholactones. Anomalous Cyclization of an Epoxytridecadienoic Acid

James D. White* , Mark S. Jensen
  • *Department of Chemistry, Oregon State University, Corvallis, OR 97331-4003, USA, Fax 503 737-2660; Internet whitej@ccmail.orst.edu
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Publication Date:
31 December 2000 (online)

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(11R,12R)-(5Z,8E)- and (11R,12R)-(5Z,8Z)-11,12-Epoxy-13-hydroxy-5,8-tridecadienoic acids were synthesized from 3-butyn-1-ol and were shown to cyclize to the δ-lactone of (12S)-(7E,10E)-5,12,13-trihydroxy-7,10-tridecadienoic acid with stannic chloride in nitromethane.

Marine metabolite - eicosanoid - asymmetric epoxidation - cyclopropane - δ-lactone

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