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.
[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.
Yasuhara
Tomohisa
T
School of Pharmaceutical Sciences, Kinki University, 3-4-1 Kowakae, Higashi-osaka, Osaka 577-8502, Japan.
Nishimura
Katsumi
K
Yamashita
Mitsuaki
M
Fukuyama
Naoshi
N
Yamada
Ken-Ichi
K
Muraoka
Osamu
O
Tomioka
Kiyoshi
K
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
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D004952:Esters; C412290:lycorane; D009584:Nitrogen