TY - JOUR
T1 - Conversion of the Enzymatically Derived (1 S,2 S)-3-Bromocyclohexa-3,5-diene-1,2-diol into Enantiomerically Pure Compounds Embodying the Pentacyclic Framework of Vindoline
AU - White, Lorenzo V.
AU - Banwell, Martin G.
N1 - Publisher Copyright:
© 2016 American Chemical Society.
PY - 2016/2/19
Y1 - 2016/2/19
N2 - 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. (Chemical Equation Presented).
AB - 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. (Chemical Equation Presented).
UR - http://www.scopus.com/inward/record.url?scp=84959018007&partnerID=8YFLogxK
U2 - 10.1021/acs.joc.5b02788
DO - 10.1021/acs.joc.5b02788
M3 - Article
SN - 0022-3263
VL - 81
SP - 1617
EP - 1626
JO - Journal of Organic Chemistry
JF - Journal of Organic Chemistry
IS - 4
ER -