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Synlett 1996; 1996(9): 913-915
DOI: 10.1055/s-1996-5601
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An Efficient Stereocontrolled Synthesis of (-)-Stypoldione

Antonio Abad1 , Consuelo Agulló, Manuel Arnó2 , Ana C. Cuñat, Benjamín Meseguer, Ramón J. Zaragozá
  • 1Departamento de Química Orgánica, Universitat de Valencia, Dr. Moliner 50, 46100-Burjassot (Valencia), Spain, Fax 34-6-3864328, E-mail: Antonio.Abad@uv.es
  • 2Departamento de Química Orgánica, Universitat de Valencia, Dr. Moliner 50, 46100-Burjassot (Valencia), Spain, Fax 34-6-3864328
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Publication History

Publication Date:
31 December 2000 (online)

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An efficient synthesis of (-)-stypoldione (3), via (-)-stypoldiol (1), was accomplished starting from S-(+)-carvone (4) using an IMDA reaction, a sonochemical Barbier reaction and an acid-catalysed quinol-tertiary alcohol cyclization as key synthetic steps.

Stypoldiol - stypoldione - carvone - spirobenzodihydrofuran - IMDA