Synlett 2001; 2001(6): 0769-0772
DOI: 10.1055/s-2001-14601
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Approach Towards the Total Synthesis of Rhizoxin: Enantioselective Preparation of the Lactone Core

Marie-Ange N'Zoutani* , Ange Pancrazi, Janick Ardisson
  • *Laboratoire de Synthèse Organique Sélective et Chimie Organométallique, CNRS-UCP-ESCOM, FRE 2126, Département de Chimie, Bat E, 13 Bd de l'Hautil, 95092 Cergy-Pontoise Cedex, France; Fax (33) 1 30 75 60 15; E-mail: j.ardisson@escom.fr; a.pancrazi@escom.fr
Further Information

Publication History

Publication Date:
31 December 2001 (online)

The construction of the C1 - C10 lactone core of rhizoxin, a 16-membered antitumoral macrolide, is reported. The strategy is based on the installation of the C7 and C8 asymmetric centers with a Brown allylation reaction. The C5 asymmetric carbon was controlled during a lactonisation step, leading to the equatorial chain at C5. Homologation sequences at C3 and C9 were performed via a Wadsworth-Emmons and a Takai reaction, respectively.

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