American Chemical Society
ol049583y_si_001.pdf (238.68 kB)

Pd-Catalyzed Carbonylative Lactamization:  A Novel Synthetic Approach to FR900482

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journal contribution
posted on 2004-05-27, 00:00 authored by Barry M. Trost, Michael K. Ameriks
An asymmetric synthesis of the benzazocine core of FR900482 has been achieved in 15 steps from 3,5-dinitro-p-toluic acid. Key features of the synthesis include an enantioselective N-methylephedrine-mediated zinc acetylide addition to a highly enolizable arylacetaldehyde and a novel Pd-catalyzed carbonylative lactamization to form an eight-membered ring.