Efficient Synthesis of the AC Ring System of Daphnilactone B

doi:10.6023/cjoc201811017

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

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Daphnilactone B的AC环系高效合成

张焱^a,b, 郭联东^b, 徐晶^b

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 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 Yan^a,b, Guo Liandong^b, Xu Jing^b

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 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).

1. Efficient Synthesis of the AC Ring System of Daphnilactone B.PDF(1192KB)

Abstract

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

Cite this article

Zhang Yan, Guo Liandong, Xu Jing. Efficient Synthesis of the AC Ring System of Daphnilactone B[J]. Chin. J. Org. Chem., 2019, 39(4): 1079-1084.

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Daphnilactone B的AC环系高效合成

Efficient Synthesis of the AC Ring System of Daphnilactone B

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