Facile and selective metalation of 7-dehydrocholesterol (pro-vitamin D3)

Successive treatment of 7-dehydrocholesterol (I) with Me3SiCH2K in THF, dry ice, mineral acid, and diazomethane gives a regioisomerically pure, homoconjugated ester II as a diastereomeric mixt., the minor component of which is thermodynamically more stable than the conjugated isomer III. [on SciFinder (R)]


Published in:
Tetrahedron Letters, 25, 14, 1449-52
Year:
1984
Keywords:
Note:
CAN 101:111260
32-7
Steroids
Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz.
Journal
0040-4039
written in English.
91667-58-2 Role: RCT (Reactant), RACT (Reactant or reagent) (metalation-carboxylation of, regiochem. of); 91667-60-6P; 91667-61-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and base-catalyzed isomerization of); 91667-59-3P; 91740-66-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and esterification of); 91667-62-8P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)
Laboratories:




 Record created 2006-03-03, last modified 2018-01-27


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