1233010-08-6Relevant academic research and scientific papers
Enantiospecific formal total synthesis of (+)-fawcettimine
Jung, Michael E.,Chang, Jonah J.
supporting information; experimental part, p. 2962 - 2965 (2010/09/15)
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 Heathcocks 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.
