
TY  - JOUR
A1  - Martyn, Derek C. 
A1  - Hoult, Deborah A. 
A1  - Abell, Andrew D. 
T1  - Stereocontrol of the Horner-Wadsworth-Emmons Reaction: Application to the Synthesis of HIV-1 Protease Inhibitors
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 2001
VL  - 54
IS  - 6
SP  - 391
EP  - 396
KW  - 
UR  - https://doi.org/10.1071/CH01093 
N2  - A systematic study on the Horner&#8211;Wadsworth&#8211;Emmons (HWE) reaction has shown that ethyl diphenylphosphonoacetate and methyl diphenylphosphonoacetate give a high excess of (Z)-alkenes. These reaction conditions were then used to prepare (Z)-ethyl-5-phenylpent-2-enoate, the corresponding (E)-isomer being prepared by standard Wittig chemistry. Reduction of each allylic ester, with diisobutylaluminium hydride (DIBAL), gave the allylic alcohols (15) and (19), respectively. Epoxidation of (15) and (19), under Sharpless conditions, gave separate samples of all four stereoisomers of 2,3-epoxy-5-phenylpentan-1-ol. Esterification of each isomer with Cbz-valine, under Mitsunobu conditions, provided (9)&#8211;(12) which were assayed against HIV protease. The cis series (9)&#8211;(10) proved to be significantly more potent than the trans (11)&#8211;(12) and, within each of these series, the isomers derived from L-diisopropyltartrate &#91;(9) and (11)&#93; were the most active. 
ER  -

