Total Synthesis of (-)-Cephalotaxine and (-)-Homoharringtonine via Furan Oxidation-Transannular Mannich Cyclization.

Angew Chem Int Ed Engl

Department of Chemistry, Oregon State University, 153 Gilbert Hall, Corvallis, OR, 97331, USA.

Published: May 2019

Homoharringtonine and its congener cephalotaxine were synthesized. Oxidative ring-opening of a furan unveils an amine-tethered dicarbonyl, which undergoes spontaneous transannular Mannich cyclization. The cascade builds the full cephalotaxine substructure in a single operation in 60 % yield. A Noyori reduction enabled synthesis of the title compounds with excellent enantioselectivity (k =278).

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http://dx.doi.org/10.1002/anie.201902174DOI Listing

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