Biomimetic syntheses of rubialatins A, B and related congeners.
The first total syntheses of rubialatins A and B, two newly discovered naphthohydroquinone dimers, were achieved with high efficiency and elegancy through rationally designed biomimetic approaches. The tandem ring contraction/Michael addition/aldol reaction followed by oxidation enabled the rapid access of prerubialatin from readily available precursors, which then diverted into rubialatins A and B via epoxidation and photoinduced skeletal rearrangement, respectively. Moreover, several new rubialatin congeners were also obtained along the synthetic tour, some of which were proved to be authentic natural products.
Hongzhi
H
Yang
Juan
J
Feng
Yuanhe
Y
Li
‡Collaborative Innovation Center for Biotherapy, Tsinghua University, Beijing 100084, China.|§Collaborative Innovation Center for Biotherapy, State Key Laboratory of Biotherapy and Cancer Center, West China Hospital, West China Medical School, Sichuan University, Chengdu 610041, China.
Yefeng
Y
Tang
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D006873:Hydroquinones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D045470:Rubia / Q000737:chemistry; D013237:Stereoisomerism
D001688:Biological Products; D006873:Hydroquinones; C000594801:rubialatin A; C000594803:rubialatin B