(S)-γ-hydroxymethyl-α,β-butenolide (aka HBO), a Valuable Chiral Synthon: Syntheses, Reactivity and Applications
Résumé
Chirality is greatly sought for pharmaceutical compounds or fragrance and flavors. (S) -γ-hydroxymethyl-α,β-butenolide, aka HBO, is a chiral (5H)-furanone providing a polarized double bond, a lactone ring and a primary alcohol as playground for synthetic chemists. This molecule has been used for forty years in a wide range of synthetic pathways to natural and/or bioactive molecules. Its own synthesis, always from biosourced product, has also significantly evolved and could be now achieved both at large scale and by applying Green Chemistryprinciples. This review will explore the syntheses, the reactivity and the uses of HBO.
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