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Synlett 1995; 1995(SI): 467-474
DOI: 10.1055/s-1995-5298
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Progress toward the Synthesis of Sarain A

Clayton H. Heathcock* , Martin Clasby, David A. Griffith, Brad R. Henke, Matthew J. Sharp
  • *Department of Chemistry, University of California, Berkeley, CA 94720, Fax 510 643-9480; Internet cch@alkaloid.cchem.berkeley.edu
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Publication Date:
31 December 2000 (online)

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In this Account we describe our efforts over more than five years to find a synthetic route to saran A (1), a complex marine alkaloid. The basic synthetic plan (Scheme 1) calls for construction of the tricyclic ”core”, annulation of the saturated 13-membered ring, and finally, annulation of the unsaturated 14-membered ring. Synthesis of the core has almost been achieved, and a suitable route has been found to lactam 103, a model for the unsaturated 14-membered ring in sarain A.

alkaloids - 1,3-dipolar cycloaddition - azomethine ylide