Synthesis of Hainanolidol and Harringtonolide

  • Author: ChemistryViews
  • Published: 14 August 2013
  • Copyright: Wiley-VCH Verlag GmbH & Co. KGaA
  • Source / Publisher: Journal of the American Chemical Society/American Chemical Society (ACS)
  • Associated Societies: American Chemical Society (ACS), USA
thumbnail image: Synthesis of Hainanolidol and Harringtonolide

Harringtonolide (pictured), hainanolidol, and fortunolides A and B are representative members of Cephalotaxus norditerpenes. Harringtonolide and related natural products may have therapeutic potential as anticancer agents.

Weiping Tang and colleagues, University of Wisconsin, Madison, USA, developed a new synthetic route for hainanolidol and harringtonolide. The tetracyclic carbon skeleton of hainanolidol and harringtonolide was efficiently constructed by an intramolecular oxidopyrylium-based [5+2] cycloaddition. An anionic ring-opening strategy was developed for the cleavage of the ether bridge in 8-oxabicyclo[3.2.1]octenes derived from the [5+2] cycloaddition. Conversion of cycloheptadiene to tropone was realized by a sequential [4+2] cycloaddition, Kornblum−DeLaMare rearrangement, and double elimination.

This new synthetic route offers the flexibility to access other members of Cephalotaxus norditerpenes and various simplified analogues.

Article Views: 3543

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