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A concise synthesis of ent-Cholesterol.

ABSTRACT: ent-Cholesterol was synthesized in 16 steps from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol.

SUBMITTER: Belani JD

PROVIDER: S-EPMC2729551 | biostudies-literature | 2008 Apr

REPOSITORIES: biostudies-literature

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A concise synthesis of ent-Cholesterol.

Belani Jitendra D JD Rychnovsky Scott D SD

The Journal of organic chemistry 20080313 7

ent-Cholesterol was synthesized in 16 steps from commercially available (S)-citronellol. The overall yield for the synthesis was 2.0%. This route is amenable to gram-scale preparation of ent-cholesterol. Isotopic incorporation near the end of the synthesis was achieved using labeled methyl iodide. This synthesis is the most practical to date and will make ent-cholesterol more readily available to use as a probe of the function and metabolism of cholesterol. ...[more]

PMID: 18336043

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