Concise Synthesis of (-)-isoaltholactone and (±)-5-epi-OBn-Goniotriol

IF 1.8 3区 化学 Q3 CHEMISTRY, ORGANIC Synthetic Communications Pub Date : 2024-06-02 DOI:10.1080/00397911.2024.2355474
Yu-Jang Li , Cheng-Chiao Li , Chung-Chien Hou
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Abstract

Concise route for the synthesis of (-)-isoaltholactone and (±)-5-epi-OBn-Goniotriol were described. Key features for the (-)-isoaltholactone synthesis involved; a) diastereoselective and enantioselective aldol reaction between chiral pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde afforded highly stereoselective syn δ-lactone, b) allylic 1,3-strain controlled epoxidation of styryl alkene following the stereospecific opening of the epoxide assisted by a proximal benzyloxy group completed the synthesis. Reaction of simple pyrrolidine substituted γ-benzyloxy vinylogous urethane enolate and cinnamaldehyde gave anti δ-lactone. Epoxidation and epoxide opening of the styryl alkene substrate of anti δ-lactone derivative was also investigated, which led to the synthesis of (±)-5-epi-OBn-Goniotriol.

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(-)-isoaltholactone 和 (±)-5- epi -OBn-Goniotriol 的简易合成
描述了合成 (-)-isoaltholactone 和 (±)-5-epi-OBn-Goniotriol 的简明路线。(-)-isoaltholactone 合成的主要特征包括a) 手性吡咯烷取代的γ-苄氧基乙烯基聚氨酯烯酸盐与肉桂醛发生非对映选择性和对映体选择性醛醇反应,得到高度立体选择性的合成δ-内酯;b) 在近端苄氧基的辅助下,苯乙烯烯的环氧化物立体特异性开放后,烯丙基 1,3-应变控制的环氧化作用完成了合成。简单的吡咯烷取代γ-苄氧基乙烯基聚氨酯烯酸盐和肉桂醛反应生成了抗δ-内酯。此外,还研究了抗δ-内酯衍生物的苯乙烯烯底物的环氧化和环氧化物开放,从而合成了(±)-5-epi-OBn-Goniotriol。
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来源期刊
Synthetic Communications
Synthetic Communications 化学-有机化学
CiteScore
4.40
自引率
4.80%
发文量
156
审稿时长
4.3 months
期刊介绍: Synthetic Communications presents communications describing new methods, reagents, and other synthetic work pertaining to organic chemistry with sufficient experimental detail to permit reported reactions to be repeated by a chemist reasonably skilled in the art. In addition, the Journal features short, focused review articles discussing topics within its remit of synthetic organic chemistry.
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