General and efficient strategy for erythrinan and homoerythrinan alkaloids: syntheses of (+/-)-3-demethoxyerythratidinone and (+/-)-erysotramidine.
[reaction: see text] A general and efficient strategy to both aromatic-type and nonaromatic-type erythrinan and homoerythrinan alkaloids has been developed. This approach involves a key two-step sequence, an alkylation of a ketone with various N-substituted iodoacetamides followed by a N-acyliminium ion promoted intramolecular cyclization, and represents one of the shortest routes to erythrinan and homoerythrinan alkaloids. As the application, the formal total synthesis of (+/-)-3-demethoxyerythratidinone and the total synthesis of (+/-)-erysotramidine have been achieved, respectively.
Gao
Shuanhu
S
State Key Laboratory of Applied Organic Chemistry & Department of Chemistry, Lanzhou University, PRC.
Tu
Yong Qiang
YQ
Hu
Xiangdong
X
Wang
Shaohua
S
Hua
Rongbao
R
Jiang
Yijun
Y
Zhao
Yuming
Y
Fan
Xiaohui
X
Zhang
Shuyu
S
D000470:Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D004895:Erythrina / Q000737:chemistry; D006576:Heterocyclic Compounds, 4 or More Rings / Q000138:chemical synthesis* / Q000737:chemistry; D026121:Indole Alkaloids / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
C514302:3-demethoxyerythratidinone; D000470:Alkaloids; D006576:Heterocyclic Compounds, 4 or More Rings; D026121:Indole Alkaloids; C492626:erysotramidine