ORGN 22 |
| Alan Whitehead and Paul R. Hanson. Department of Chemistry, University of Kansas, 1251 Wescoe Hall Dr, Lawrence, KS 66045 |
| The synthetic utility of nonracemic phosphorus heterocycles (P-heterocycles) produced via ring-closing olefin metathesis (RCM) will be presented. We have demonstrated that phosphorus can be utilized for the rapid functionalization of RCM-generated cyclic allyl phostone motifs en route to P-chiral phosphonosugars. We now report a terminus differentiation strategy utilizing RCM for the desymmetrization of 1,3-anti-diols employing a phosphorus tether. The resulting bicyclic phosphorus framework contains a number of salient features, including endo- and exocyclic olefins for further synthetic manipulation and a temporary phosphorus tether (P-tether). The primary goal of this project is to evaluate the efficacy of these P-heterocyclic building blocks in application towards the development of 1,3-diol-containing synthons for target-directed synthesis. Initial efforts in our group are aimed at the heptalactone feigrisolide B. Feigrisolide B has been found to demonstrate high levels of antibacterial activity as well as moderate cytotoxic and antiviral properties. |
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New Reactions and Methodology
8:00 AM-12:00 PM, Sunday, March 28, 2004 Anaheim Convention Center -- 303A, Oral
Division of Organic Chemistry |