Regeneration of Pinusolide from Its 17-Nor-8-oxo Derivative

  • Han, Byung-Hoon (Natural Products Research Institute, Seoul National University) ;
  • Song, Wan-Jin (Natural Products Research Institute, Seoul National University, Sookmyung Women′s University) ;
  • No, Kwnag-Hyun (Sookmyung Women′s University)
  • Published : 1997.06.01

Abstract

For metabolic study of pinusolide, a naturally occurring platelet activating factor antagonist, a synthetic method for preparation of radiolabeled pinusolide was studied. Pinusolide was first oxidized with $OsO_4/NaIO_4 $to 17-nor-8-oxo compound (2), which was subsequently converted to pinusolide by treatment with the Lombardo reagent $(Zn/CH_2Br_2/TiCI_4)$. The Wittily reaction was unsuccessful in the latter carbonyl methylenation of 2.

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