Multi-functional phosphorus heterocycles: An RCM/X-MET sequence to polyol subunits

ORGN 117

Joshua D. Waetzig, jwaetzig@ku.edu, Alan Whitehead, alanwh@ku.edu, and Paul R. Hanson, phanson@ku.edu. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Drive, Lawrence, KS 66045
The described method focuses on tripodal coupling of allylic alcohols to a phosphate tether and ensuing ring-closing metathesis (RCM) to provide a unique P-chiral bicyclic phosphate possessing a differentiated 1,3-anti-diol subunit. Cross-metathesis (X-MET) with an array of functionalized olefins using Hoveyda-Grubbs catalyst affords additional diversification of the external olefin. Further exploitation of the phosphate tether, taking advantage of its latent leaving/protecting group capabilities, provides useful subunits with application towards natural product synthesis.

 

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