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

被引：0
作者：
Li, Yu-Jang [1 ]
Li, Cheng-Chiao [1 ]
Hou, Chung-Chien [1 ]
机构：
[1] Natl Chiayi Univ, Dept Appl Chem, 300 Univ Rd, Chiayi City 60004, Taiwan
来源：
SYNTHETIC COMMUNICATIONS | 2024年 / 54卷 / 11期
关键词：
Isoaltholactone; aldol reaction; vinylogous urethane enolate; delta-lactone; SELECTIVE ALDOL REACTIONS; STEREOSELECTIVE-SYNTHESIS; VINYLOGOUS URETHANE; BIOACTIVE STYRYLLACTONES; FORMAL SYNTHESIS; (+)-ALTHOLACTONE; (+)-GONIOTRIOL; LACTONES; CYTOTOXICITY; CONSTITUENTS;
D O I：
10.1080/00397911.2024.2355474
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
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 gamma-benzyloxy vinylogous urethane enolate and cinnamaldehyde afforded highly stereoselective syn delta-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 gamma-benzyloxy vinylogous urethane enolate and cinnamaldehyde gave anti delta-lactone. Epoxidation and epoxide opening of the styryl alkene substrate of anti delta-lactone derivative was also investigated, which led to the synthesis of (+/-)-5-epi-OBn-Goniotriol.
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页码：918 / 926
页数：9
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