A convenient entry to C2- and C3-substituted gulono-gamma-lactone derivatives from L-ascorbic acid.
A convenient entry to C2- and C3-substituted gulono-gamma-lactone derivatives from L-ascorbic acid.
复制标题
方便地从 L-抗坏血酸中获得 C2-和 C3-取代的古洛糖酸-γ-内酯衍生物。
DOI：
10.1021/jo0508550
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发表时间：
2005
期刊：
影响因子：
--
通讯作者：
Wimalasena,Kandatege
中科院分区：
文献类型：
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作者：
Olabisi,AyodeleO;Mahindaratne,MathewPD;Wimalasena,Kandatege
本文介绍了一种从l-抗坏血酸出发制备未知手性C2-和C3-官能化的醛酮基-1，4-内酯衍生物的简便方法，该方法在合成用于结构-活性研究的各种手性活性剂衍生物中具有重要价值。通过分别使用5，6-O-异亚丙基-1-抗坏血酸的相应3-O-和2-O-烯丙基衍生物的热克莱森重排来合成一系列5，6-O-异亚丙基-2-烯丙基-3-酮基-1-半乳糖酸-γ-内酯和5，6-O-异亚丙基-3-烯丙基-2-酮基-1-半乳糖酸-γ-内酯衍生物，证明了该方法的实用性，然后立体定向还原成相应的醇。合成步骤被证明是有效的，和对映体特异性，他们进行高产率。
A convenient method to obtain unknown chiral C2- and C3-functionalized aldono-1,4-lactone derivatives starting froml-ascorbic acid, which would be valuable in the synthesis of derivatives of various pharmacologically active agents for structure−activity studies, is described. The practicality of this approach is demonstrated by the synthesis of a series of 5,6-O-isopropylidene-2-allyl-3-keto-l-galactono-γ-lactone and 5,6-O-isopropylidene-3-allyl-2-keto-l-galactono-γ-lactone derivatives using the thermal Claisen rearrangement of the corresponding 3-O- and 2-O-allyl derivatives of 5,6-O-isopropylidene-l-ascorbic acid, respectively, followed by stereospecific reduction to the corresponding alcohols. The synthetic steps are shown to be efficient, and enantiospecific, and they proceed with high yields.