Total synthesis of lycorine-type alkaloids by cyclopropyl ring-opening rearrangement.
A practical method for the synthesis of lycorine-type alkaloids with cis-B/C ring structure has been developed. Based on the reactions of aminocyclization, palladium-mediated arylation and especially cyclopropyl ring-opening rearrangement, the synthesis of anhydrocaranine, (±)-γ-lycorane and putative (±)-amarbellisine was accomplished.
Key Laboratory of Medicinal Chemistry for Natural Resource (Yunnan University), Ministry of Education, School of Chemical Science and Technology, Yunnan University, Kunming, Yunnan 650091, P. R. China. jpliu@ynu.edu.cn.
Dandan
D
Liu
Long
L
Ai
Fan
F
Li
Annan
A
Zhao
Jingbo
J
Chen
Hongbin
H
Zhang
Jianping
J
Liu
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D047151:Amaryllidaceae Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D066241:Carbon-13 Magnetic Resonance Spectroscopy; D018360:Crystallography, X-Ray; D003500:Cyclization; D010617:Phenanthridines / Q000138:chemical synthesis* / Q000737:chemistry; D066244:Proton Magnetic Resonance Spectroscopy
D000470:Alkaloids; D047151:Amaryllidaceae Alkaloids; D010617:Phenanthridines; C580729:amarbellisine; C412290:lycorane; C015330:lycorine