
TY  - JOUR
A1  - Collins, DJ 
T1  - The structure and function of oestrogens. V. Synthesis of (9,12,12-<sup>2</sup>H<sub>3</sub>)- and (11&#950; 12,12-<sup>2</sup>H<sub>3</sub>)-oestradiol
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1983
VL  - 36
IS  - 2
SP  - 403
EP  - 407
KW  - 
UR  - https://doi.org/10.1071/CH9830403 
N2  - 17,17-Ethylenedioxy-3-methoxy(9,12,12-2H3)-9&#946;-oestra-l,3,5(10)-trien-11-one (3) was reduced to the mixture of 11-epimeric alcohols (4) which upon elimination of DHO gave the (12,12-2H2)-9(11)- dehydrooestrone derivative (5b). Treatment of (5b) with (2H6)diborane followed by oxidation afforded the (9,12,12-2H3)alcohol (8a); hydride reduction of the corresponding tosylate then gave 17,17-ethylenedioxy-3-methoxy(9,12,12-2H3)oestra-l,3,5(l0)-triene (7). Acid hydrolysis of (7), followed by demethylation, and reduction with sodium borohydride yielded (9,12,12-2H3)oestradiol (10). Sodium borohydride reduction of (11&amp;12,12-2H3)oestrone (6),prepared in several steps from the 9&#946;,12,12-trideutero ketone (3), gave (11 &#958;,12,12-2H3)oestradiol (9). [The two trideuterated oestradiols (9) and (10) were required for biological studies.] 
ER  -

