The absolute configuration of (+)-3,4-Bis(p-hydroxyphenyl)hexane (hexoestrol) and related compounds

Abstract

(+)-(2S,3R)-2,3-Bis(p-methoxyphenyl)valeric acid, previously converted into (-)-(2R,3R)-2,3-bis(p-methoxyphenyl)pentane, has now been converted into (+)-(3R,4R)-3,4-bis(p-methoxyphenyl)hexane via (+)-(3S,4R)-3,4-bis(p-methoxyphenyl)hexan-2-one and (-)-(4s)-3,4-bis(p-methoxypheny1)hex-2-ene. This provides unequivocal correlation of the absolute stereochemistry of a series of homologous diarylalkanes, and a corresponding series of diarylalkenes.