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Published on: June 13, 2022
Enantiospecific formal total synthesis of (+)-fawcettimine
Michael E Jung1, Jonah J Chang
1Department of Chemistry and Biochemistry, University of California, Los Angeles, 405 Hilgard Avenue, Los Angeles, California 90095, USA. jung@chem.ucla.edu
Abstract:
The diastereospecific attack of the silyl enol ether on the activated cyclopropyl diester 27 generated the hydrindanone 28 with complete stereocontrol. Thermal decarbomethoxylation of 28 gave the monoester 29, a key intermediate in Heathcock's synthesis, thereby completing a formal total synthesis of (+)-fawcettimine 1. The analogous cyclization of 33, the diastereomer of 27, afforded the diastereomeric diester 34, thereby demonstrating that the cyclization process is diastereospecific.
