Intramolecular bromo-amination of 1,4-cyclohexadiene aminal: one-pot discrimination of two olefins and concise asymmetric synthesis of (-)-gamma-lycorane.
The reaction of cyclohexa-2,5-dienyl-1-methylaldehyde and optically pure 1,2-diaryl-1,2-diamine followed by intramolecular bromo-amination produced a one-pot discrimination of two olefins in the cyclohexane system, which was used for the asymmetric synthesis of (-)-gamma-lycorane.
Graduate School of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka, 565-0871, Japan. fujioka@phs.osaka-u.ac.jp
Hiromichi
H
Fujioka
Kenichi
K
Murai
Yusuke
Y
Ohba
Hideki
H
Hirose
Yasuyuki
Y
Kita
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis*; D000586:Amination; D001966:Bromine / Q000737:chemistry*; D053138:Cyclohexenes / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy
D047151:Amaryllidaceae Alkaloids; D053138:Cyclohexenes; C412290:lycorane; C048401:1,4-cyclohexadiene; D001966:Bromine