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Synthesis of a 2,7-Dioxatricyclo[4.2.1.0^3,8]nonane: A Model Study for Possible Application in a Synthesis of Dictyoxetane

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Kelly A. Marshall, Anna K. Mapp, and Clayton H. Heathcock*

Department of Chemistry, University of CaliforniaBerkeley, Berkeley, California 94720

J. Org. Chem., 1996, 61 (26), pp 9135–9145

DOI: 10.1021/jo961680k

Publication Date (Web): December 27, 1996

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

Abstract

A method for the synthesis of the 2,7-dioxatricyclo[4.2.1.0^3,8]nonane ring system characteristic of the marine diterpene dictyoxetane has been developed. This method utilizes a dipolar cycloaddition of a 3-oxidopyrylium salt to create the carbon skeleton (Scheme 1) and employs an intramolecular S_N2 displacement to form the oxetane ring (Schemes 9, 10, 13). The route described could easily be adapted to incorporate additional functionality, making it potentially useful in a total synthesis of dictyoxetane.

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Published In Issue December 27, 1996
Received August 30, 1996

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Article

Synthesis of a 2,7-Dioxatricyclo[4.2.1.0^3,8]nonane: A Model Study for Possible Application in a Synthesis of Dictyoxetane