Levoglucosenone is a chiral α,β-unsaturated ketone that can be efficiently synthesized from cellulosic biomass through acid flash pyrolysis. This highly dehydrated sugar has been used previously in the preparation of chiral synthons such as (-)-y-multistriatin and (+)-Prelog-Djerassi lactonic acid. Recently, levoglucosenone has been efficiently converted into pure (S)-γ-hydroxymethyl-α,β-butenolide (HBO), a chiral chemical platform suited for the synthesis of drugs, flavors and antiviral agents. This presentation will describe the optimization of the synthesis of HBO from levoglucosenone as well as some chemo-enzymatic transformations of HBO into valuable chiral fine chemicals such as flavors, chiral epoxides and rare sugars.

Chemo-enzymatic syntheses of chiral epoxides, rare sugars and flavors from levoglucosenone-derived (S)-γ-Hydroxymethyl-α,β-Butenolide (HBO)

253rd National Meeting (2017)

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