Ruthenium-SYNPHOS-Catalyzed Asymmetric Hydrogenations: an Entry to Highly Stereoselective Synthesis of the C15− C30 Subunit of Dolabelide A

C Roche, N Desroy, M Haddad, P Phansavath…

Index: Roche, Christophe; Desroy, Nicolas; Haddad, Mansour; Phansavath, Phannarath; Genet, Jean-Pierre Organic Letters, 2008 , vol. 10, # 17 p. 3911 - 3914

Full Text: HTML

Citation Number: 21

Abstract

ABSTRACT An efficient construction of the C15-C30 segment of the cytotoxic macrolide dolabelide A is described. The synthesis relies on ruthenium-SYNPHOS-mediated asymmetric hydrogenation reactions of β-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio-and diastereoselectivity.