Synthesis of Tricolorin F

Marco Brito-Arias, Rogelio Pereda-Miranda, and Clayton H. Heathcock*
Center for New Directions in Organic Synthesis, Department of Chemistry, University of California, Berkeley, California 94720, Unidad Profesional Interdisciplinaria de Biotecnologa, Instituto Politnico Nacional, Av. Acueducto s/n Barrio La Laguna Ticomn, Mexico City 07340, Mexico, and Departamento de Farmacia, Facultad de Qumica, Universidad Nacional Autonoma de Mxico, Ciudad Universitaria, Mexico City 04510, Mexico
J. Org. Chem., 2004, 69 (14), pp 4567–4570
DOI: 10.1021/jo030244c
Publication Date (Web): January 6, 2004
Copyright © 2004 American Chemical Society
*

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

, heathcock@cchem.berkeley.edu

Abstract

Abstract Image

A hetero-trisaccharide resin glycoside of jalapinolic acid known as tricolorin F has been synthesized. The approach involved the preparation of intermediate 5 and a subsequent coupling reaction with imidate 6 to produce disaccharide 7, which after deacetylation generated intermediate 8. A further coupling between this glycosyl acceptor and the quinovose glycosyl donor 9 resulted in the formation of the tricoloric acid C derivative 10. Basic hydrolysis afforded the intermediate 11, which was subsequently lactonized under Yamaguchi conditions to produce protected macrolactone 12. Removal of acetonide and benzyl protecting groups afforded pure tricolorin F (1).

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History

  • Published In Issue July 09, 2004
  • Received July 29, 2003

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