We have previously reported a synthesis utilizing ring-closing metathesis to form seven-membered heterocycles containing sulfur, nitrogen, and phosphorous, known as a thiol phosphonamidate. Herein we report an optimized methodology, and an amino acid-based diversification method of these heterocycles. Our progress using two amino acid derivative routes will be discussed.  The first route utilizes valine and leucine to externally diversify the heterocycle at nitrogen. The second route provides diversification within the heterocycle by utilizing substituted allyl amines produced via Wittig chemistry. Using these synthetic strategies, we intend to make a library of potential biologically active heterocycles.

Synthetic approaches to thiol phosphonamidate derivatives

247th National Meeting (2014)

The official archive and repository for all ACS Meetings & Expositions abstracts and select posters or presentations.