The synthesis of isoquinoline alkaloid and its related compounds using alanine derivatives as chiral auxiliaries.
Chiral 1-substituted isoquinoline derivatives, which were obtained by the reaction using alanine derivatives as chiral auxiliaries, were transformed to (S)-2,3,9,10,11-pentamethoxyhomoprotoberberine (7) and a synthetic intermediate for O-methylkreysigine (9) in good yields and high stereoselectivity. The corresponding chiral allyl derivative of isoquinoline was transformed to a pyrrolidinoisoquinoline (16) in a highly enantioselective manner.
Itoh
Takashi
T
School of Pharmaceutical Sciences, Showa University, Tokyo, Japan.
Nagata
Kazuhiro
K
Yokoya
Masashi
M
Miyazaki
Michiko
M
Kameoka
Keiko
K
Nakamura
Shigeru
S
Ohsawa
Akio
A
D000409:Alanine / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000470:Alkaloids / Q000138:chemical synthesis*; D007546:Isoquinolines / Q000138:chemical synthesis*; D013237:Stereoisomerism; D013678:Technology, Pharmaceutical / Q000379:methods
D000470:Alkaloids; D007546:Isoquinolines; D000409:Alanine