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Paper | Regular issue | Vol 36, No. 9, 1993, pp.2073-2080
Published online, 1st January, 1970
DOI: 10.3987/COM-93-6423
Synthesis of (-)-Heliotridane and (-)-Isoretronecanol via Diastereoselective Conjugate Addition of Organocuprates to an Enoate Deriving from Proline

Sylvie Le Coz, André Mann,* Frédéric Thareau, and Maurizio Taddei

*Laboratoire de Pharmacochimie Moléculaire, Centre de Neurochimie du CNRS, 5, rue Blaise Pascal, 67084 Strasbourg Cedex, France

Abstract

A syntesis of the pyrrolizidine alkaloids (-)-heliotridane and (-)-isoretronecanol and their epimers is described. The key step involves a diastereoselective conjugate addition of organocuprates to (2S)-N-(tert-butoxycarbonyl)-2-[(E)-3’-methoxy-3’-oxo-1’-propenyl]pyrrolidine (2) deriving from (S)-proline.