Synfacts 2011(8): 0813-0813  
DOI: 10.1055/s-0030-1260755
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag Stuttgart ˙ New York

Synthesis of (±)-Cycloclavine and (±)-5-epi-Cycloclavine

Contributor(s): Steven V. Ley, Kimberley A. Roper
F. R. Petronijevic, P. Wipf*
University of Pittsburgh, USA
Further Information

Publication History

Publication Date:
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).