Efforts toward the asymmetric total synthesis of pyranicin

ORGN 182

Danielle Jacobs, dljacobs@email.unc.edu, Department of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599 and Michael T Crimmins, Venable and Kenan Laboratories of Chemistry, University of North Carolina at Chapel Hill, Chapel Hill, NC 27599-3290.
Recent efforts towards the asymmetric total synthesis of pyranicin, a member of the Annonaceous acetogenin family of natural products, will be illustrated. The unique mode of reactivity of the Annonaceous acetogenins, which exhibits direct dependence upon the diversely oxygenated structure, makes them attractive candidates as multi-drug resistant cancer therapies. The Crimmins laboratory has developed and optimized a powerful and versatile asymmetric glycolate aldol ring-closing metathesis (RCM) strategy to access such medium-size ring ethers of varying substitution and configuration as those found in the Annonaceous acetogenins. The tetrahydropyranyl ring will be accessed via this aldol-RCM technology, and the aliphatic backbone will be constructed via a late-stage Carreira-type coupling that concurrently installs the C10 asymmetric hydroxyl group.

 

New Reactions and Methodology, Materials, Total Synthesis, Process R&D
8:00 PM-10:00 PM, Sunday, 28 August 2005 Washington DC Convention Center -- Hall A, Poster

Sci-Mix
8:00 PM-10:00 PM, Monday, 29 August 2005 Washington DC Convention Center -- Hall A, Sci-Mix

Division of Organic Chemistry

The 230th ACS National Meeting, in Washington, DC, Aug 28-Sept 1, 2005