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A new method for the preparation of ent-cholesterol from ent-testosterone

โœ Scribed by A.Sampath Kumar; Douglas F. Covey

Publisher
Elsevier Science
Year
1999
Tongue
French
Weight
218 KB
Volume
40
Category
Article
ISSN
0040-4039

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โœฆ Synopsis

An efficient total synthesis of the enantiomer of cholesterol is reported. The enantiomer of testosterone was prepared and converted into a C21 3-silyloxy-ASJ7(zยฐ)-diene according to literature procedures. The additional five carbon atoms of the cholesterol side chain were introduced by an ene reaction. Selective hydrogenation of the resultant A 16 double bond and removal of the 22-hydroxyl group by a mesylation and demesylation sequence gave ent-cholesterol in 9.7% overall yield from ent-testosterone

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