title: A novel and practical route to A-ring enyne synthon for 1 alpha,25-dihydroxyvitamin D3 analogs: synthesis of A-ring diastereomers of 1 alpha,25-dihydroxyvitamin D2 and 3-methyl-1,25-dihydroxyvitamin D3.
abstract: A novel and practical route to the A-ring enyne synthon (2), which can be versatile for a variety of A-ring analogs of 1 alpha,25-dihydroxyvitamin D3 (1), was developed. This novel method led to an improved synthesis of the A-ring diastereomers of 1, the compounds 13-15, and synthesis of the new analogs, 2-methyl-1,25-dihydroxyvitamin D3 (4) with its all possible diastereomers. The biological evaluation of the 2-methyl analogs showed the alpha alpha beta-isomer to be more potent than 1.
authors.affiliation: Faculty of Pharmaceutical Sciences, Teikyo University, Kanagawa, Japan.
authors.forename: K
authors.initials: K
authors.lastname: Konno
authors.forename: S
authors.initials: S
authors.lastname: Maki
authors.forename: T
authors.initials: T
authors.lastname: Fujishima
authors.forename: Z
authors.initials: Z
authors.lastname: Liu
authors.forename: D
authors.initials: D
authors.lastname: Miura
authors.forename: M
authors.initials: M
authors.lastname: Chokki
authors.forename: H
authors.initials: H
authors.lastname: Takayama
mesh_terms: D002117:Calcitriol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D014807:Vitamin D / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry / Q000494:pharmacology
chemical_list: C116441:2-methyl-1,25-dihydroxyvitamin D3; D014807:Vitamin D; D002117:Calcitriol