Tackling reactivity and selectivity within a strained architecture: construction of the [6-6-5-7] tetracyclic core of Calyciphylline alkaloids.
A stereochemically controlled route to the enantiopure [6-6-5-7] tetracyclic core of Calyciphylline A class alkaloids was established, which involves Overman rearrangement, [2 + 2] photochemical cycloaddition, Grob fragmentation, C-N bond-forming nucleophilic displacement, and ring strain-directed hydrogenation as strategic steps.
Laboratory of Chemical Genomics, School of Chemical Biology and Biotechnology, Shenzhen Graduate School of Peking University, Shenzhen University Town, Nanshan District, Shenzhen 518055, China.
Chen
C
Xu
Lu
L
Wang
Xiaojiang
X
Hao
David Zhigang
DZ
Wang
D003500:Cyclization; D008968:Molecular Conformation; D055668:Photochemical Processes; D011083:Polycyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry
D011083:Polycyclic Compounds; C479143:calyciphylline A