First Total Synthesis of 11-Thia Steroids

Frédéric Cachoux; Malika Ibrahim-Ouali; Maurice Santelli

doi:10.1055/s-2000-6534

Synlett 2000; 2000(3): 418-420
DOI: 10.1055/s-2000-6534

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First Total Synthesis of 11-Thia Steroids

Frédéric Cachoux^* , Malika Ibrahim-Ouali, Maurice Santelli

^*Laboratoire de Synthèse Organique associé au CNRS (ESA 6009), Faculté des Sciences de Saint Jérôme, 13397 Marseille Cedex 20, France; E-mail: m.santelli@lso.u-3mrs.fr/m.ibrahim@lso.u-3mrs.fr

Abstract

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An efficient synthesis of 11-thia steroids was achieved via an intramolecular Diels-Alder cycloaddition of orthoquinodimethane as the key step. The major isomer was transformed into sulfoxide 7. The vinyl group of the steroid 7 has been oxidized using the Wacker process to the corresponding ketone 8 in good yield.

thia steroid - intramolecular Diels-Alder - orthoquinodimethane - sulfoxide - Wacker oxidation

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