Chin. J. Org. Chem. ›› 2019, Vol. 39 ›› Issue (4): 1079-1084.DOI: 10.6023/cjoc201811017 Previous Articles     Next Articles

Articles

Daphnilactone B的AC环系高效合成

张焱a,b, 郭联东b, 徐晶b   

  1. a 哈尔滨工业大学化学与化工学院 哈尔滨 150001;
    b 南方科技大学化学系与深圳格拉布斯研究院 深圳 518055
  • 收稿日期:2018-11-12 修回日期:2018-12-05 出版日期:2019-04-25 发布日期:2018-12-21
  • 通讯作者: 郭联东, 徐晶 E-mail:xuj@sustc.edu.cn;guold@sustc.edu.cn
  • 基金资助:

    国家自然科学基金(No.21772082)、深圳市科技创新委员会基础研究学科布局项目和孔雀技术创新(Nos.JCYJ20170817110515599,KQJSCX2017072815423320)、深圳市发改委(学科建设扶持计划)、深圳市孔雀团队(No.KQTD20150717103157174)和深圳市诺贝尔奖实验室计划(No.C17783101)资助项目.

Efficient Synthesis of the AC Ring System of Daphnilactone B

Zhang Yana,b, Guo Liandongb, Xu Jingb   

  1. a School of Chemistry and Chemical Engineering, Harbin Institute of Technology, Harbin 150001;
    b Department of Chemistry and Shenzhen Grubbs Institute, Southern University of Science and Technology, Shenzhen 518055
  • Received:2018-11-12 Revised:2018-12-05 Online:2019-04-25 Published:2018-12-21
  • Contact: 10.6023/cjoc201811017 E-mail:xuj@sustc.edu.cn;guold@sustc.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No.21772082),the Shenzhen Science and Technology Innovation Committee Basic Research Discipline Layout Project and Peacock Technology Innovation (Nos.JCYJ20170817110515599,KQJSCX2017072815423320),the Shenzhen De-velopment and Reform Commission (Discipline Construction Program),the Shenzhen Peacock Plan (No.KQTD20150717103157174) and the Shenzhen Nobel Prize Scientists Laboratory Project (No.C17783101).

The synthesis of the AC ring moiety of daphnilactone B has been achieved through an efficient Diels-Alder reaction and Au-catalyzed Conia-ene reaction in seven steps with 30% overall yield. Our strategies paved the way to the total synthesis of various daphnilactone B-type Daphniphyllum alkaloids.

Key words: daphniphyllum alkaloid, daphnilactone B, Diels-Alder reaction, Conia-ene reaction, total synthesis