Synthesis of catechins via thiourea/AuCl(3)-catalyzed cycloalkylation of aryl epoxides.
A diversity-oriented approach for the synthesis of structurally diverse catechins was achieved in good yields via thiourea/AuCl(3)/AgOTf-catalyzed annulations of aryl epoxides under mild conditions. This new protocol provides a highly efficient entry to a library of catechins-derived natural products, notably anti-HIV agent 8-C-ascorbyl-(-)-epigallocatechin.
Liu
Yongxiang
Y
Key Laboratory of Bioorganic Chemistry and Molecular Engineering of Ministry of Education and Beijing National Laboratory for Molecular Science (BNLMS), School of Pharmaceutical Science, Peking University, Beijing, China.
Li
Xiben
X
Lin
Guang
G
Xiang
Zheng
Z
Xiang
Jing
J
Zhao
Mingzhe
M
Chen
Jiahua
J
Yang
Zhen
Z
D000478:Alkylation; D002384:Catalysis; D002392:Catechin / Q000138:chemical synthesis*; D003500:Cyclization; D004852:Epoxy Compounds / Q000737:chemistry*; D017612:Gold Compounds / Q000737:chemistry*; D009682:Magnetic Resonance Spectroscopy; D021241:Spectrometry, Mass, Electrospray Ionization; D013890:Thiourea / Q000737:chemistry*
D004852:Epoxy Compounds; D017612:Gold Compounds; C038016:gold chloride; D002392:Catechin; D013890:Thiourea