Total synthesis of the monoterpenoid indole alkaloid (±)-aspidophylline A.
Aspidophylline A belongs to the akuammiline alkaloid family, the members of which possess intriguing cagelike structures and diverse biological activities. Herein we report a 15-step synthesis of this alkaloid from conveniently available starting materials. The key elements of the synthesis include an intramolecular oxidative coupling to create the tetracyclic furoindoline motif of the natural product and a [Ni(cod)2 ]-mediated cyclization to install its piperidine ring.
State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032 (P.R. China).
Mingxing
M
Teng
Weiwei
W
Zi
Dawei
D
Ma
D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006576:Heterocyclic Compounds, 4 or More Rings; C584601:aspidophylline A
monoterpene indole alkaloids; natural products; nickel; oxidative coupling; total synthesis