In an effort to expand the scope of the intramolecular C—S bond-forming process, developed by Robertson et. al., and to access other highly privileged, sulfur-containing scaffolds this chemistry shall be thoroughly investigated. The development of a synthetic method that describes the synthesis of 2-substituted dithianes shall be fully explored due to the biological significance of this structural motif. The common intermediate O,O-diethyl S-(2-((2-(methoxy(methyl)amino)-2-oxoethyl)thio)ethyl) phosphorothioate, which is the linchpin of this project, was originally accessed in mediocre yields. However, the individual steps of the protocol have recently been successfully optimized so that yields of &gt;90% were realized. Now that a robust protocol for the synthesis of the common intermediate, O,O-diethyl S-(2-((2-(methoxy(methyl)amino)-2-oxoethyl)thio)ethyl) phosphorothioate, has been developed the synthesis of the 1,4-dithiane moiety will be pursued so that a comprehensive library of 1,4-dithianes can be compiled.

New approach to the synthesis of 1,4-dithianes

255th National Meeting (2018)

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