Total syntheses of racemic, natural (-) and unnatural (+) glyceollin I.
The first total syntheses of racemic glyceollin I and its enantiomers are described. A Wittig approach was utilized as an entry to the appropriately substituted isoflav-3-ene so that an osmium tetroxide mediated asymmetric dihydroxylation could be deployed for stereospecific introduction of the 6a-hydroxy group. While using triphenylphosphine hydrobromide, a novel method was found for gently removing MOM from protected phenolic hydroxyl groups present within sensitive systems.
Khupse
Rahul S
RS
Department of Medicinal and Biological Chemistry, Center for Drug Design and Development, The University of Toledo, Toledo, Ohio 43606-3390, USA.
Erhardt
Paul W
PW
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D036343:Pterocarpans / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D036343:Pterocarpans; C017343:glyceollin