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

The Journal of Organic Chemistry
Lorenzo V White, Martin G Banwell

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.

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Citations

May 14, 2016·Natural Product Reports·Robert A Hill, Andrew Sutherland
Mar 25, 2018·Angewandte Chemie·JiaJia DongWuyuan Zhang
Dec 6, 2017·Chemical Record : an Official Publication of the Chemical Society of Japan ... [et Al.]·Ehab S TaherPing Lan
Jan 14, 2021·Organic & Biomolecular Chemistry·Cristina Preston-HerreraJordan T Froese
Jul 17, 2018·Accounts of Chemical Research·Faiyaz KhanMartin G Banwell
Sep 14, 2017·Organic Letters·Mihail KazakEdgars Suna

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