有机化学 ›› 2019, Vol. 39 ›› Issue (9): 2671-2675.DOI: 10.6023/cjoc201903014 上一篇    下一篇

研究简报

3-去羟基Phomonol的合成

叶青青a, 张梦帆a, 刘耀宗b, 杨震a   

  1. a 绍兴文理学院 浙江省精细化工与传统工艺绿色替代技术重点实验室 绍兴 312000;
    b 甘肃银光聚银化工有限公司 白银 730900
  • 收稿日期:2019-03-08 修回日期:2019-04-18 出版日期:2019-09-25 发布日期:2019-04-26
  • 通讯作者: 杨震 E-mail:yangzhen09@usx.edu.cn
  • 基金资助:

    国家自然科学青年基金(No.21302129)和浙江省自然科学基金(No.LQ13B020002)资助项目.

Synthesis of 3-Dehydroxyphomonol

Ye Qingqinga, Zhang Mengfana, Liu Yaozongb, Yang Zhena   

  1. a Zhejiang Key Laboratory of Alternative Technologies for Fine Chemicals Process, Shaoxing University, Shaoxing 312000;
    b Gansu Yinguang Juyin Chemical Co., Ltd, Baiyin, Gansu 730900
  • Received:2019-03-08 Revised:2019-04-18 Online:2019-09-25 Published:2019-04-26
  • Contact: 10.6023/cjoc201903014 E-mail:yangzhen09@usx.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 21302129) and the Natural Science Foundation of Zhejiang Province (No. LQ13B020002).

以商业购买的(R)-3-羟基-4-氯丁酸乙酯或者(S)-1,2-环氧戊烷为原料,经过6步反应,完成了天然产物类似物3-去羟基phomonol的合成,关键步骤包括格氏反应,Prins环化反应和钯催化分子内烷氧羰基化反应等,无保护基合成策略的应用缩短了合成步骤,提高了合成的效率.

关键词: 合成, 3-去羟基phomonol, Prins环化反应, 钯催化分子内烷氧羰基化反应

A concise synthesis of 3-dehydroxyphomonol has been accomplished in six steps from commercially available (R)-4-chloro-3-hydroxy-butyric acid ethyl ester or (S)-2-propyl-oxirane. The key steps involved Grignard reaction, Prins cyclization and palladium-catalyzed intramolecular alkoxycarbonylation to install the tetrahydropyran ring. The synthesis demonstrated an application of protecting-group-free strategy.

Key words: synthesis, 3-dehydroxyphomonol, Prins cyclization, palladium-catalyzed intramolecular alkoxycarbonylation