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Synlett 2001; 2001(3): 0349-0352
DOI: 10.1055/s-2001-11401
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A Simple Synthetic Approach to Trachylobane, Beyerane, and Atisane Diterpenoids from Carvone

Antonio Abad* , Consuelo Agulló, Ana C. Cuñat, Ismael Navarro, M. Carmen Ramírez de Arellano
  • *Departamento de Química Orgánica, Universitat de Valencia, Dr. Moliner 50, 46100-Burjassot (Valencia), Spain; Fax + 34(6)3 86 43 28; E-mail: Antonio.Abad@uv.es
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Publication Date:
31 December 2001 (online)

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A stereoselective general synthetic approach to trachylobane-, beyerane-, and atisane-type polycyclic diterpenoids from carvone is described. Key steps in this approach are an IMDA reaction, an intramolecular diazo ketone cyclopropanation of an unsaturated ketone, and a controlled regioselective opening of a cyclopropyldiketone moiety.

terpenoids - Diels-Alder reaction - diazo compounds - ring opening - cyclopropane