title: Fluoride-mediated elimination of allyl sulfones: application to the synthesis of a 2,4-dimethyl-A-ring vitamin D3 analogue.
abstract: A coupling strategy for the synthesis of 2,4-dimethyl-1α,25(OH)(2)D(3) is achieved which involves methylation of a pro-A ring vinyl sulfone and in situ traping of the allyl sulfonyl anion with a CD ring allyl chloride. TBAF-promoted 1,2-eliminative desulfonylation and concomitant silyl ether deprotection gives the vitamin D(3) analogue.
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, United States.
authors.forename: Vikas
authors.initials: V
authors.lastname: Sikervar
authors.forename: James C
authors.initials: JC
authors.lastname: Fleet
authors.forename: Philip L
authors.initials: PL
authors.lastname: Fuchs
mesh_terms: D000498:Allyl Compounds / Q000737:chemistry*; D002117:Calcitriol / Q000138:chemical synthesis* / Q000737:chemistry*; D002762:Cholecalciferol / Q000031:analogs & derivatives* / Q000138:chemical synthesis* / Q000737:chemistry*; D005459:Fluorides / Q000737:chemistry*; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*; D014753:Vinyl Compounds / Q000737:chemistry*
chemical_list: D000498:Allyl Compounds; D013450:Sulfones; D014753:Vinyl Compounds; D002762:Cholecalciferol; D002117:Calcitriol; D005459:Fluorides; C023698:allyl chloride