title: Intramolecular methylation of an allyl sulfone via lithium alkoxyaluminate; application to the enantioselective synthesis of the CD ring of vitamin D3.
abstract: Alcohol-directed intramolecular methylation of an enantiopure allyl sulfone using AlMe(3) provides a trans-hydrindane CD ring alcohol. The substrate cis-CD ring allyl sulfone alcohol is prepared via intramolecular allyl sulfonyl anion addition to aldehyde using Ba(OH)(2).
authors.affiliation: Department of Chemistry, Purdue University, West Lafayette, Indiana 47907, USA.
authors.forename: Vikas
authors.initials: V
authors.lastname: Sikervar
authors.forename: Philip L
authors.initials: PL
authors.lastname: Fuchs
mesh_terms: D002762:Cholecalciferol / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D008745:Methylation; D015394:Molecular Structure; D013237:Stereoisomerism; D013450:Sulfones / Q000737:chemistry*
chemical_list: D013450:Sulfones; D002762:Cholecalciferol; D008094:Lithium