
TY  - JOUR
A1  - Collins, DJ 
A1  - Hobbs, JJ 
T1  - Antioestrogenic and antifertility compounds. III. Enantiomers of (&#177;)-hexoestrol and its homologues
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1970
VL  - 23
IS  - 8
SP  - 1605
EP  - 1624
KW  - 
UR  - https://doi.org/10.1071/CH9701605 
N2  - (±)-2,3-Bis(p-hydroxyphenyl)butane (5a) and (&amp;)-3,4-bis(p-hydroxyphenyl)-hexane (5c) were resolved, and absolute stereochemistry of the former was established as (-)-(2R,3R) by correlation with (+)-(R)-2,3-bis(p-methoxyphenyl)but-1-en. The (+) and (-) isomers of erythro-2,3-bis(p-hydroxyphenyl)pentane (Sb) were synthesized from (-)- and (+)-erythro-2,3-bis(p-methoxyphenyl)valeric acid, respectively. (+)-erythro-2,3-Bis(p-hydroxyphenyl)pentane (5b) was shown to have the (2R,3S) configuration, and (+)-threo-(b) the (2S,3S) configuration, by correlation with (-)-(8)-2,3-bis(p-methoxyphenyl)pent-1-ene. It follows that the configuration of erythro-2,3-bis(p-methoxyphenyl)-valeric and the corresponding-butyric acid is (+)-(2S,3R). Interaction of optically active hexoestrol and its homologues with the oestrogen receptor active site is discussed in terms of steroid stereochemistry. 
ER  -

