TY - JOUR
AU1 - Bunnage, Mark E.
AU2 - Davies, Stephen G.
AU3 - Goodwin, Christopher J.
AB - A practical and efficient asymmetric synthesis of the 3-benzoylamino-2-hydroxy-3-phenylpropionic acid derived side chain of the important anticancer agent taxol is described. The pivotal synthetic transformation relies upon the highly diastereoselective tandem lithium amide conjugate addition–electrophilic hydroxylation of -butyl cinnamate . The resultant β-amino-α-hydroxy acid derivative is readily converted to the  diastereoisomer of the taxol side chain methyl ester, from which the naturally occurring  configuration is secured by a simple Mitsunobu inversion sequence  a dihydrooxazole intermediate. Under optimal conditions, this straightforward approach provides the taxol side chain methyl ester (–)-(natural enantiomer) in four steps and 60% yield from -butyl cinnamate . The protocol is applied to the preparation of all four taxol side chain stereoisomers and is extended to allow for the synthesis of the side chain of taxotére, a potent taxol analogue.
TI - Asymmetric synthesis of the taxol and taxotère C-13 side chains
JF - Journal of the Chemical Society, Perkin Transactions 1
DO - 10.1039/p19940002385
DA - 1994-01-01
UR - https://www.deepdyve.com/lp/royal-society-of-chemistry/asymmetric-synthesis-of-the-taxol-and-taxot-re-c-13-side-chains-wdviVsu6Vm
SP - 2385
EP - 2391
VL - 
IS - 17
DP - DeepDyve
ER -