Diastereoselective Synthesis of syn-Alkanetriols from a Glyceral Derivative via k-Selectride Reduction: Application to the Synthesis of a Pheromone of the Sugarcane Weevils

Abstract

k-selectride reduction of commercially available d-mannitol­ derived ketones 2b-i produced the corresponding alcohols 3b-i in good yields and with absolute syn-selectivity in almost all the cases. It was proposed that the bulky cyclohexylidene moiety of 3 has a significant role in favoring the reduction with k-selectride via Felkin-Anh model. Subsequently, one of the reduction product 3c has been exploited to synthesize the pheromone I of sugarcane weevil.

k-selectride - reduction - syn-alkanetriols - selectivity - Felkin-Anh model

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