Abstract
The asymmetric total synthesis of arbornamine was accomplished in 13 steps, leading to the assignment of its absolute configuration. The key features of the strategy include construction of the C16 quaternary carbon center by a highly diastereoselective Grignard reagent addition to N-tert-butanesulfinylimine, sequential site-selective amidation and N-alkylation to form the C and E rings, and [Ni(COD)2]-mediated Michael addition to close the D ring.
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