
TY  - JOUR
A1  - Collins, DJ 
A1  - Hobbs, JJ 
T1  - Some transformations of 6&#945;-Bromocholest-4-en-3&#946;-ol and its 3-Acetate. A convenient synthesis of 3,6-Dialkoxysteroids
JF  - Australian Journal of Chemistry
JO  - Aust. J. Chem.
Y1  - 1964
VL  - 17
IS  - 6
SP  - 677
EP  - 691
KW  - 
UR  - https://doi.org/10.1071/CH9640677 
N2  - The term "ambiallylic" is introduced to describe the system -C-C=C-C- in which X and Y are functional groups. The novel reactivity of some ambiallylic systems, including 6a-bromocholest-4-en-3&#946;-ol and its 3-acetate, is discussed. During chromatography over Florisil 6&#945;-bromocholest-4-en-3&#946;-ol was con- verted to a mixture of cholest-4-en-3-one, cholest-5-en-3-one, and cholest-4-ene- 3&#946;,6&#946;-diol, together with other unidentified products. Chromatography of 6&#945;-bromo- cholest-4-en-3&#946;-ol 3-acetate over Florisil led to extensive decomposition; the only product identified was cholest-5-ene-3&#946;,4&#946;-diol 4-acetate. Treatment of 6&#945;-bromocholest-4-en-3&#946;-ol 3-acetate with methanol or ethanol containing pyridine gave 6&#945;-methoxy- or 6&#946;-ethoxy-cholest-4-en-3&#946;-ol 3-acetate, which upon further reaction with methanol or ethanol containing hydrochloric acid afforded 3&#946;,6&#946;-dimethoxy-, 3&#946;-ethoxy-6&#946;-methoxy-, 3&#946;-methoxy-6&#946;-ethoxy-, or 3&#946;,6&#946;-diethoxy-cholest-4-ene, respectively. 
ER  -

