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Synlett 1997; 1997(5): 574-576
DOI: 10.1055/s-1997-3217
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First Diastereoselective Synthesis of (-)-Thyrsiflorin A Methyl Ester

Antonio Abad, Consuelo Agulló, Manuel Arnó, M. Luisa Marín, Ramón J. Zaragozá*
  • *Departament de Química Orgánica, Facultat de Química, Universitat de València, E-46100 Burjassot (València), Spain, Fax 34-6-3864328; E-mail: Ramon.J.Zaragoza@uv.es
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Publication Date:
31 December 2000 (online)

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The diastereoselective synthesis of the simplest member of the scopadulan diterpenes, (-)-thyrsiflorin A methyl ester 10 from chiral (+)-podocarp-8(14)-en-13-one 1, of known absolute configuration, is described. A key step in our synthesis is the intramolecular cyclopropanation of the diazoketone 5 and subsequent regioselective cleavage of the cyclopropane ring.

diastereoselective synthesis - Scopadulan diterpenes - cyclopropane cleavage - podocarpenone

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