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

ORGN 117

Joshua D. Waetzig,, Alan Whitehead,, and Paul R. Hanson, 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

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