Rapid assembly of the polyhydroxylated b-amino acid constituents of microsclerodermins C, D et E.

Thomas Hjelmgaard (1) , Sophie Faure (1) , P. Lemoine (2) , B. Viossat (2) , David J Aitken (3)

1 SEESIB - Synthèse et étude de systèmes à intêret biologique
2 LCRB - UMR 8015 - Laboratoire de cristallographie et RMN biologiques
3 ICMMO - Institut de Chimie Moléculaire et des Matériaux d'Orsay

A very short and efficient synthesis of protected derivatives of APTO and AETD, the complex polyhydroxylated -amino acid residues present in microsclerodermins C, D, and E, is described. The targets are obtained in only five steps, in 23% and 16% overall yields, respectively. The key transformation involves the completely diastereoselective two-carbon homologation of appropriately selected intermediate chiral sulfinimines

Domaines: Chimie organique

Thomas Hjelmgaard, Sophie Faure, P. Lemoine, B. Viossat, David J Aitken. Rapid assembly of the polyhydroxylated b-amino acid constituents of microsclerodermins C, D et E.. Organic Letters, 2008, 10, pp.841-844. ⟨hal-00265269⟩