title: Total synthesis of (+/-)-alpha- and beta-lycoranes by sequential chemoselective conjugate addition-stereoselective nitro-Michael cyclization of an omega-nitro-alpha,beta,psi,omega-unsaturated ester.
abstract: [reaction: see text] An omega-nitro-alpha,beta,psi,omega-unsaturated ester underwent a chemoselective conjugate addition of a nitroolefin moiety with aryllithium to produce a psi-aryl-omega-nitro-alpha,beta-unsaturated ester, which was then stereoselectively cyclized by intramolecular nitro-Michael reaction giving a functionalized cyclohexane applicable to the total synthesis of (+/-)-alpha- and beta-lycoranes.
authors.affiliation: School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, 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: Mitsuaki
authors.initials: M
authors.lastname: Yamashita
authors.forename: Naoshi
authors.initials: N
authors.lastname: Fukuyama
authors.forename: Ken-Ichi
authors.initials: K
authors.lastname: Yamada
authors.forename: Osamu
authors.initials: O
authors.lastname: Muraoka
authors.forename: Kiyoshi
authors.initials: K
authors.lastname: Tomioka
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids; D003500:Cyclization; D004952:Esters / Q000737:chemistry*; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D004952:Esters; C412290:lycorane; D009584:Nitrogen