title: Conversion of the Enzymatically Derived (1S,2S)-3-Bromocyclohexa-3,5-diene-1,2-diol into Enantiomerically Pure Compounds Embodying the Pentacyclic Framework of Vindoline.
abstract: The enzymatically derived and enantiomerically pure (1S,2S)-3-bromocyclohexa-3,5-diene-1,2-diol (7) has been elaborated over 17 steps into compounds 8 and 32, each of which embodies the pentacyclic framework and much of the functionality associated with the alkaloid vindoline (3). This work sets the stage for effecting the conversion of the related metabolite (1S,6R)-5-ethyl-1,6-dihydroxycyclohexa-2,4-diene-1-carboxylic acid (4) into compound 3, the latter being a biogenetic precursor to the clinically significant anticancer agents vinblastine and vincristine.
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Lorenzo V
authors.initials: LV
authors.lastname: White
authors.affiliation: Research School of Chemistry, Institute of Advanced Studies, The Australian National University , Canberra, ACT 2601, Australia.
authors.forename: Martin G
authors.initials: MG
authors.lastname: Banwell
mesh_terms: D000470:Alkaloids / Q000737:chemistry*; D000970:Antineoplastic Agents / Q000737:chemistry* / Q000494:pharmacology; D001969:Bromobenzenes / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D013237:Stereoisomerism; D014747:Vinblastine / Q000031:analogs & derivatives* / Q000737:chemistry* / Q000494:pharmacology; D014750:Vincristine / Q000737:chemistry* / Q000494:pharmacology
chemical_list: D000470:Alkaloids; D000970:Antineoplastic Agents; D001969:Bromobenzenes; D053138:Cyclohexenes; C009667:vindoline; D014750:Vincristine; D014747:Vinblastine; C041284:3-bromo-3,5-cyclohexadiene-1,2-diol