Portal de Periódicos da CAPES

Enantiomerically pure γ-butyrolactones in natural products synthesis

1995; Elsevier BV; Linguagem: Inglês

10.1016/s1572-5995(06)80065-7

2542-6621

Stacie S. Canan Koch, A. Richard Chamberlin,

Chemical synthesis and alkaloids

Stereochemically defined γ-butyrolactones have served as key building blocks in the syntheses of many types of natural products, including alkaloids, macrocyclic antibiotics, lignan lactones, pheromones, anti-leukemics, and flavor components. Accordingly, there are a large number of methods for the enantioselective preparation of substituted γ-butyrolactones: from simple natural products such as amino acids, tartaric acid, ascorbic acids, carbohydrates, or ribonolactones; from chiral sulfoxides, epoxides, or substituted acetylenic acids; and by various enzymatic or synthetic reductions, oxidations, and hydrolyses. This review will summarize these enantioselective methods of lactone synthesis and for each briefly show how the resultant lactone fits into the synthetic scheme for a particular natural product synthesis.