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Total Synthesis of Sinensilactam A
Wenbin Shao1, Jun Huang1, Kai Guo1
1State Key Laboratory of Chemical Oncogenomics, Key Laboratory of Chemical Genomics , Peking University Shenzhen Graduate School , Shenzhen 518055 , China.
Abstract:
The total synthesis of naturally occurring (±)-sinensilactam A was achieved in 18 steps. The key steps of this work are a rhodium-catalyzed [3 + 2] cycloaddition for construction of the two all-carbon vicinal quaternary centers and a convergent and tandem condensation of the in situ generated N-acyliminium intermediate with aldehyde 20. This enabled implementation of a unified strategy for stereoselective formation of the tetracyclic hemiaminal core of sinensilactam A in a later stage. The total syntheses of applanatumol F and C8- epi-applanatumol D are also achieved using this strategy.
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