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.
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.
Yasuhara
Tomohisa
T
School of Pharmaceutical Sciences, Kinki University, Higashi-osaka, Osaka 577-8502, Japan.
Nishimura
Katsumi
K
Osafune
Emi
E
Muraoka
Osamu
O
Tomioka
Kiyoshi
K
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*
D003510:Cyclohexanes; D004952:Esters; D009942:Organometallic Compounds; C450681:phenyllithium; D009584:Nitrogen