Planta Med 2012; 78 - PK4
DOI: 10.1055/s-0032-1321320

Asymmetric synthesis of Pterolinus D derivatives

SF Wu 1, FR Chang 1, YC Wu 1, 2, KH Lee 3
  • 1Graduate Institute of Natural Products, Kaohsiung Medical University, Kaohsiung, Taiwan
  • 2School of Chinese Medicine, College of Chinese Medicine, China Medical University, Taichung, Taiwan
  • 3Natural Products Research Laboratories, UNC Eshelman School of Pharmacy, University of North Carolina, Chapel Hill

Pterolinus D was an active component of anti-inflammatory activity and cytotoxicity from Pterocarpus santalinus. Herein, an asymmetric synthesis of pterolinus D derivatives (7a-b, 7'a-7'b) was processed by Evans chiral auxiliary methodology to introduce a methyl stereogenic center, followed by Friedel-Crafts reaction and LiAlH4 reduction to give an hydroxyl stereogenic center as a Cram isomer. The structures are confirmed by NMR, MS and CD-ORD spectroscopy methods.