Concerning the chemical synthesis of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one, a novel regulator of cholesterol metabolism.
A four-step synthesis of 3 beta-hydroxy-5 alpha-cholest-8(14)-en-15-one (I) from 7-dehydrocholesterol is described. This synthesis, which is efficient and suitable for kilogram scale work, was carried out in a 33% overall average yield (39% overall best yield). A major byproduct of the hydrolysis of 3 beta-benzoyloxy-14 alpha,15 alpha-epoxy-5 alpha-cholest-7-ene to I was found to be the ring C aromatic sterol 12-methyl-18-nor-5 alpha-cholesta-8,11,13-trien-3 beta-ol. Several other intermediates and byproducts of these reactions were also identified. All new sterols were characterized by 1H- and 13C-NMR.
Wilson
W K
WK
Department of Biochemistry, Rice University, Houston, Texas 77251.
Wang
K S
KS
Kisic
A
A
Schroepfer
G J
GJ
D002782:Cholestenes / Q000138:chemical synthesis* / Q000378:metabolism; D002783:Cholestenones / Q000138:chemical synthesis*; D002784:Cholesterol / Q000378:metabolism*; D006868:Hydrolysis; D009682:Magnetic Resonance Spectroscopy; D009654:Norsteroids / Q000138:chemical synthesis
D002782:Cholestenes; D002783:Cholestenones; D009654:Norsteroids; C015073:cholest-8(14)-en-3-ol-15-one; C058199:3-benzoyloxy-14,15-epoxycholest-7-ene; C058200:12-methyl-18-norcholesta-8,11,13-trien-3-ol; D002784:Cholesterol