Synthetic Applications of the Thermal Rearrangement of Ozonides: First Enantiospecific Synthesis of Marine Metabolite Luffarin W

Alejandro F. Barrero; E. J. Alvarez-Manzaneda; Rachid Chahboun; J. M. Cuerva; A. Segovia

doi:10.1055/s-2000-7150

Synlett 2000; 2000(9): 1269-1272
DOI: 10.1055/s-2000-7150

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Synthetic Applications of the Thermal Rearrangement of Ozonides: First Enantiospecific Synthesis of Marine Metabolite Luffarin W

Alejandro F. Barrero^* , E. J. Alvarez-Manzaneda, Rachid Chahboun, J. M. Cuerva, A. Segovia

^*Departamento de Química Orgánica, Facultad de Ciencias, Universidad de Granada, 18071 Granda, Spain; Fax +34 58 24 33 18; E-mail: afbarre@goliat.ugr.es

Abstract

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The ozonides on quaternary carbons undergo thermal rearrangement to yield a mixture of formates and alkenes. This reaction constitutes an alternative procedure to the unusual Baeyer-Villiger rearrangement of aliphatic aldehydes. The first enantiospecific synthesis of the marine metabolite Luffarin W from (-)-sclareol has been carried out, based on this methodology.

ozonolysis - Baeyer-Villiger rearrangement - aldehydes - nor-terpenes

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