title: Synthesis of nitrogen-functionalized cyclohexanes using chemoselective conjugate addition of phenyllithium to linear omega-nitro-alpha,beta,psi,omega-unsaturated ester and subsequent stereoselective intramolecular nitro-Michael cyclization.
abstract: Nitrogen-functionalized cyclohexane derivatives with three contiguous chiral centers were synthesized by nitroalkene-selective conjugate addition of phenyllithium to a omega-nitro-alpha,beta,psi,omega-unsaturated ester and subsequent stereocontrolled intramolecular nitro-Michael cyclization with cesium fluoride and a quaternary ammonium bromide. The cyclohexanes were applicable to the total synthesis of alpha-, beta- and gamma-lycoranes.
authors.affiliation: School of Pharmaceutical Sciences, Kinki University, Higashi-osaka, Osaka 577-8502, Japan.
authors.forename: Tomohisa
authors.initials: T
authors.lastname: Yasuhara
authors.forename: Katsumi
authors.initials: K
authors.lastname: Nishimura
authors.forename: Emi
authors.initials: E
authors.lastname: Osafune
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D003500:Cyclization; D003510:Cyclohexanes / Q000138:chemical synthesis*; D004952:Esters / Q000737:chemistry*; D008968:Molecular Conformation; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry*; D009942:Organometallic Compounds / Q000737:chemistry*
chemical_list: D003510:Cyclohexanes; D004952:Esters; D009942:Organometallic Compounds; C450681:phenyllithium; D009584:Nitrogen