Asymmetric construction of quaternary carbon centers by sequential conjugate addition of lithium amide and in situ alkylation: utility in the synthesis of (-)-aspidospermidine.
Chiral diether ligand-controlled asymmetric conjugate addition of a lithium amide to cyclopentenecarboxylate and subsequent in situ alkylation gave a chiral cyclopentane derivative bearing a quaternary carbon with high enantio- and diastereoselectivity. The cyclopentane derivative was converted successfully to (-)-aspidospermidine.
Suzuki
Mayuko
M
Graduate School of Pharmaceutical Sciences, Kyoto University, Yoshida, Sakyo-ku, Kyoto 606-8501, Japan.
Kawamoto
Yoshito
Y
Sakai
Takeo
T
Yamamoto
Yasutomo
Y
Tomioka
Kiyoshi
K
D000478:Alkylation; D000577:Amides / Q000737:chemistry*; D000586:Amination; D002384:Catalysis; D003517:Cyclopentanes / Q000138:chemical synthesis / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D008094:Lithium / Q000737:chemistry*; D015394:Molecular Structure; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D000577:Amides; D003517:Cyclopentanes; D026121:Indole Alkaloids; D011804:Quinolines; C409672:aspidospermidine; D008094:Lithium