Catalytic asymmetric assembly of octahydroindolones: divergent synthesis of lycorine-type amaryllidaceae alkaloids (+)-α-lycorane and (+)-lycorine.
We report the first catalytic asymmetric approach to octahydroindolones and a divergent enantioselective synthesis of perhydroindole alkaloids, as exemplified by lycorine-type Amaryllidaceae alkaloids (+)-α-lycorane and (+)-lycorine, from a common intermediate by using a highly concise route. The assembly of octahydroindolones employs a catalytic enantioselective 1,4-conjugate addition of nitro dienynes, followed by a TsOH-catalyzed cascade synthesis of highly functionalized enones, and a diastereoselective intramolecular Michael addition.
Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091 (P.R. China), Fax: (+86) 871-65035538.
Zhongwen
Z
Sun
Mingtao
M
Zhou
Xiang
X
Li
Xueling
X
Meng
Fangzhi
F
Peng
Hongbin
H
Zhang
Zhihui
Z
Shao
D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D007211:Indoles / Q000138:chemical synthesis / Q000737:chemistry*; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D047151:Amaryllidaceae Alkaloids; D007211:Indoles; D010617:Phenanthridines; C412290:lycorane; C015330:lycorine
cascade reactions; conjugate additions; divergent total synthesis; enantioselective catalysis; octahydroindolones