Planta Med 2013; 79 - P47
DOI: 10.1055/s-0033-1336489

Concise, Stereoselective Syntheses of (+)- and (-)-Crispine A

SCK Rotte 1, AG Chittiboyina 1, IA Khan 1, 2
  • 1National Center for Natural Products Research, School of Pharmacy
  • 2Department of Pharmacognosy, The University of Mississippi, University, MS 38677

Alkaloid, (+)-Crispine A (1) was isolated from Carduus crispus in 2002; it is known to possess significant cytotoxic activity especially against SKOV3, KB and Hela human cancer cell lines1. For the first time, concise, linear and protecting group-free stereoselective syntheses of both antipodes of Crispine A have been achieved in 6 steps starting from commercially available Veratraldehyde. The full synthetic sequence involving asymmetric Keck allylation and Pummerer rearrangement as crucial transformations will be presented.

Acknowledgements: This study was supported in part by United States Department of Agriculture, Agricultural Research Service, Specific Cooperative Agreement No. 58 – 6408 – 02 – 1-612. References: [1] Zhang Q, Tu G, et al. (2002) Tetrahedron, 58: 6795 – 6798.