Synthesis 2010(10): 1649-1653  
DOI: 10.1055/s-0029-1218741
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Stereoselective Total Synthesis of (+)-Dodoneine

Florent Allais*, Paul-Henri Ducrot*
INRA UMR1318 Institut Jean-Pierre Bourgin, INRA route de Saint-Cyr, 78026 Versailles Cedex, France
Fax: +33(1)30833119; e-Mail: florent.allais@versailles.inra.fr; e-Mail: ducrot@versailles.inra.fr;
Further Information

Publication History

Received 14 January 2010
Publication Date:
19 April 2010 (online)

Abstract

A total synthesis of the naturally occurring dihydropyr­anone dodoneine is reported. The combination of a highly catalytic enantioselective allylboration and a highly diastereoselective allylstannation was used for the stereoselective generation of the two stereogenic centers. The pyranone ring was created in two steps through generation of a Z-configured α,β-unsaturated ester and lactonization via intramolecular transesterification.

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