Ruthenium-SYNPHOS-catalyzed asymmetric hydrogenations: an entry to highly stereoselective synthesis of the C15-C30 subunit of dolabelide A.
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 beta-keto esters to generate the C19, C21, and C27 hydroxyl-bearing stereocenters with very high levels of enantio- and diastereoselectivity.
Roche
Christophe
C
Laboratoire de Synthèse Sélective Organique et Produits Naturels UMR 7573 CNRS, ENSCP, 11 rue Pierre et Marie Curie, 75231 Paris Cedex 01, France.
Desroy
Nicolas
N
Haddad
Mansour
M
Phansavath
Phannarath
P
Genet
Jean-Pierre
JP
D002384:Catalysis; D004952:Esters / Q000138:chemical synthesis / Q000737:chemistry; D006865:Hydrogenation; D007659:Ketones / Q000138:chemical synthesis / Q000737:chemistry; D018942:Macrolides / Q000138:chemical synthesis*; D009942:Organometallic Compounds / Q000737:chemistry; D012428:Ruthenium / Q000737:chemistry; D013237:Stereoisomerism
D004952:Esters; D007659:Ketones; D018942:Macrolides; D009942:Organometallic Compounds; C481199:dolabelide A; D012428:Ruthenium