Khupse Rahul S, Erhardt Paul W
Department of Medicinal and Biological Chemistry, Center for Drug Design and Development, The University of Toledo, Toledo, Ohio 43606-3390, USA.
Org Lett. 2008 Nov 6;10(21):5007-10. doi: 10.1021/ol802112r. Epub 2008 Sep 26.
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.
