title: A general approach to the synthesis of enantiopure 19-nor-vitamin D3 and its C-2 phosphate analogs prepared from cyclohexadienyl sulfone.
abstract: A synthesis of enantiopure 19-nor-Vitamin D(3) and its C-2 substituted cyclic phosphate analogs is achieved via in situ trapping of an α-sulfonyl anion with a CD-ring allyl chloride and 1,2-eliminative desulfonylation exploiting the basic properties of TBAF. The A-ring is prepared via anti-selective dithiane addition to vinyl sulfone and LiBH(4) mediated sequential bis reduction of an epoxy vinyl sulfone.
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
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: D060326:Chemistry Techniques, Synthetic; D002762:Cholecalciferol / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D003510:Cyclohexanes / Q000138:chemical synthesis*; D008958:Models, Molecular; D008968:Molecular Conformation; D010710:Phosphates / Q000737:chemistry*; D013237:Stereoisomerism; D013450:Sulfones / Q000138:chemical synthesis* / Q000737:chemistry*
chemical_list: D003510:Cyclohexanes; D010710:Phosphates; D013450:Sulfones; D002762:Cholecalciferol