Total synthesis of indole alkaloid (+/-)-subincanadine F via SmI2)-mediated ring opening and bridge-forming Mannich reaction.
The first total synthesis of (+/-)-subincanadine F, a bioactive indole alkaloid structurally featuring a 1-azabicyclo[4.3.1]decane unit, has been realized from 1-(para-methoxybenzyl)tryptamine in six steps. The bridge-containing tetracyclic framework of subincanadine F was efficiently assembled by a SmI2-mediated ring opening followed by an acid-mediated Mannich reaction. In addition, the tetracyclic ketoester 6, a key intermediate potentially useful for synthesizing structurally related indole alkaloids as well, was obtained in one step from alpha,beta-diketoester 5.
Gao
Peng
P
Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai, China 200032.
Liu
Yanqin
Y
Zhang
Lei
L
Xu
Peng-Fei
PF
Wang
Shaowu
S
Lu
Yong
Y
He
Mingyuan
M
Zhai
Hongbin
H
D003500:Cyclization; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization
D026121:Indole Alkaloids; C522871:subincanadine F