Optically Pure Dihydroxy γ-Alkylated γ-Butyrolactones Starting from l-Tartaric Acid: Application to Formal and Total Syntheses of Natural Products
Optically Pure Dihydroxy γ-Alkylated γ-Butyrolactones Starting from l-Tartaric Acid: Application to Formal and Total Syntheses of Natural Products
复制标题
以l-酒石酸为原料的光学纯二羟基γ-烷基化γ-丁内酯：在天然产物的形式合成和全合成中的应用
DOI：
10.1021/jo970117e
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发表时间：
1997
影响因子：
3.6
通讯作者：
L. Duhamel
中科院分区：
文献类型：
--
作者：
Anne;J. Plaquevent;L. Duhamel
描述了从L-酒石酸（1）出发制备差向异构光学纯γ-丁内酯2和3的一般和有效的方法。众所周知，这些内酯是天然产物合成中的重要组成部分。酒石酸（1）被转化为羰基化手性酮（酮4和醛5）。当这些手性子进行高度立体选择性反应（还原或有机金属加成）时，在内酯化和脱保护步骤后产生差向异构二羟基γ-丁内酯2和3。得到的光学纯内酯是生物化合物的前体，并允许全合成的l-生物蝶呤和槲皮内酯，dodecanolactone，avenaci，和tetrahydrocerulenin的正式合成。
A general and efficient preparation of epimeric optically pure γ-butyrolactones 2 and 3 is described starting from l-tartaric acid (1). These lactones are well-known to be important building blocks in the syntheses of natural products. l-Tartaric acid (1) was transformed into carbonylated chirons (ketones 4 and aldehyde 5). These chirons, when submitted to highly stereoselective reactions (reduction or organometallic addition), led to epimeric dihydroxy γ-butyrolactones 2 and 3 after lactonization and deprotection steps. The resulting optically pure lactones are precursors of biological compounds and have allowed a total synthesis of l-biopterin and formal syntheses of quercus lactone, dodecanolactone, avenaciolide, and tetrahydrocerulenin.