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Synthesis of (±)-Cycloclavine and (±)-5-epi-Cycloclavine
F. R. Petronijevic, P. Wipf*
University of Pittsburgh, USA
20 July 2011 (online)
Cycloclavine is an indole alkaloid isolated from the African morning glory (Ipomea hildebrandtii) and possesses three contiguous stereocenters, including one which is part of a cyclopropane ring. This is the second total synthesis of (±)-cycloclavine, the first was completed by Incze et al. in 2008 in 14 steps with 0.2% overall yield (Tetrahedron 2008, 64, 2924). This synthesis revolves around an intramolecular Diels-Alder cycloaddition of a furan to close the indole ring; methodology previously published by the Wipf group (Chem. Commun. 2009, 104).