? Our work in synthesizing propargyl-linked antifolates has led to a need for an expedient synthesis of alkynes with varying substitution at the propargyl position to further our structure-activity relationship understanding.  In applying known chemistry to our system, we have developed methods to generate unsubstituted, mono-, and di-methylated alkynes from a single propargyl alcohol, with little to no isomerization to the allene and in the presence of various nitrogenous heterocycles.  This allows for facile manipulation of the propargyl alcohol, without the need for Nicholas-type protection of the alkyne.  These methods have afforded us a later stage divergence than previously available, and has expedited the synthesis of our desired inhibitors.

Deoxygenation/methylation of heteroaryl propargyl alcohols: Methods to generate unsubstituted, mono-, and di-methylated alkynes

247th National Meeting (2014)

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