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Short Paper | Regular issue | Vol 96, No. 3, 2018, pp.470-482
Published online, 13th February, 2018
DOI: 10.3987/COM-17-13858
Synthetic Studies of Yessotoxin: Stereoselective Annulation of the CD and JK Ring Fragments by Using Pd(II)-Catalyzed Cyclization

Hajime Yokoyama,* Genki Moriyama, Kazuki Nishida, Yasuhiro Kusumoto, Kiyoshi Tsuge, Masahiro Miyazawa, and Yoshiro Hirai

*Department of Chemistry, Graduate School of Science and Engineering, University of Toyama, 3190 Gofuku, Toyama 930-8555, Japan

Abstract

Yessotoxin is the polycyclic ether implicated in diarrheic shellfish poisoning. This toxin has A-K ring system involving 6-, 7-, 8-membered ether rings. We have been studying high stereoselective Pd(II)-catalyzed cyclization. Herein we describe the CD and JK ring fragments of yessotoxin by our annulation based on Pd(II)-catalyzed cyclization. The efforts to understand these high stereoselectivities are also disclosed. This annulation method could be applicable to other polyethers and related natural products.