title: Selective deoxygenation of allylic alcohol: stereocontrolled synthesis of lavandulol.
abstract: Selective deoxygenation of allylic alcohol can be successfully carried out by the formation of alkoxyalkyl ether (EE or MOM), followed by Pd(dppe)Cl(2)-catalyzed reduction with LiBHEt(3). (+)-S-Lavandulol has been efficiently synthesized by the application of this protocol to the diol derived from the Pb(OAc)(4)-promoted oxidative ring-opening of (-)-R-carvone. This deoxygenation method is general and selective for allylic alcohols.
authors.affiliation: Department of Chemistry, Myong Ji University, Yongin, Kyunggi-Do, Korea.
authors.forename: Hee Jin
authors.initials: HJ
authors.lastname: Kim
authors.forename: Liang
authors.initials: L
authors.lastname: Su
authors.forename: Heejung
authors.initials: H
authors.lastname: Jung
authors.forename: Sangho
authors.initials: S
authors.lastname: Koo
mesh_terms: D000080462:Acyclic Monoterpenes; D002384:Catalysis; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes / Q000138:chemical synthesis* / Q000737:chemistry*; D010084:Oxidation-Reduction; D010165:Palladium / Q000737:chemistry; D020005:Propanols / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D000080462:Acyclic Monoterpenes; D000081005:Cyclohexane Monoterpenes; D039821:Monoterpenes; D020005:Propanols; C006463:allyl alcohol; D010165:Palladium; C006923:carvone; C492921:lavandulol