A psico-oxetanocin analog has been synthesized from simple starting materials using carbonylation of epoxides and incorporation of a nucleobase onto 2-methyleneoxetanes as key steps. The silyl ether protected 2-methyleneoxetane gave a better overall yield than the benzoyl ester protected one. Furthermore, the reactivity and selectivity of nucleobase incorporation with both 2-methyleneoxetanes and 2-methylenetetrahydrofurans have been studied. Anchimeric assistance has been seen with 5-membered transition states, but not 6-membered.

Preparation of a <i>psico</i>-oxetanocin and investigation of the role of neighboring group participation

240th National Meeting (2010)

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Preparation of a psico-oxetanocin and investigation of the role of neighboring group participation