2002/06/04 by Xin Jiang, Douglas F. Covey · 2 citations
Medicine · Biochemistry, Genetics and Molecular Biology · Pharmacology, Toxicology and Pharmaceutics · #Cholesterol and Lipid Metabolism #Steroid Chemistry and Biochemistry #Pharmacogenetics and Drug Metabolism
paper · doi:10.1021/jo025535k
openalex publication_date 2002/06/04 · openalex created_date 2016/06/24 · openalex updated_date 2026/08/01
For the first time, one of the two enantiomers of cholesterol (ent-cholesterol) has been synthesized by a synthetic route that starts from a precursor containing the D-ring and entire side chain of cholesterol. As part of the reported synthetic route, a method of general utility for the large scale (>10 g) preparation of each enantiomer of [1 alpha(R*),7a alpha]-1-(1,5-dimethylhexyl)-1,2,3,6,7,7a-hexahydro-7a-methyl-5H-inden-5-one, C,D ring-side chain synthons that can be used for the synthesis of enantiomers of vitamin D(3), cholesterol, and their analogues was also developed. Using the enantiomer of the C,D-ring side-chain synthon that leads to ent-cholesterol, the A- and B-rings were elaborated from a linear fragment that is sequentially cyclized to form the steroid B- and A-rings. Using this route, ent-cholesterol was prepared in 23 steps from the methyl ester of (1 alpha,5 alpha,6 alpha)-(+/-)-6-methyl-2-oxo-bicyclo[3.1.0]hexane-1-carboxylic acid in a total yield of 2.6%.