Synthesis of Framework Structure of Guaiane

doi:10.6023/cjoc202009010

Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (4): 1739-1743.DOI: 10.6023/cjoc202009010 Previous Articles Next Articles

NOTES

Guaiane的骨架结构合成研究

王敏寿¹^,²^,^*(), 张洪彬¹^,²^,^*()

a 滇西应用技术大学理化教研室云南大理 671006
b 云南大学自然资源药物化学教育部重点实验室昆明 650091

收稿日期:2020-09-04 修回日期:2020-11-09 发布日期:2020-12-05
通讯作者: 王敏寿, 张洪彬

Synthesis of Framework Structure of Guaiane

Minshou Wang¹^,²^,^*(), Hongbin Zhang¹^,²^,^*()

a West Yunnan University of Applied Sciences, Department of Physics and Chemistry, Dali, Yunnan 671006
b Key Laboratory of Medicinal Chemistry for Natural Resource, Ministry of Education, Yunnan University, Kunming 650091

Received:2020-09-04 Revised:2020-11-09 Published:2020-12-05
Contact: Minshou Wang, Hongbin Zhang
About author:
* Corresponding authors. E-mail: wmshou.good@163.com;
E-mail: zhanghb@ynu.edu.cn

1. cjoc202009010辅助材料.pdf(1120KB)

Abstract

A new method for the synthesis of chiral 5,7-fused oxygen bridged ring based on Prins cyclization is reported. It provides a new way for the synthesis of the skeleton structure of guaiacane sesquiterpenes. Based on dioxinone, the synthesis of chiral 5,7-fused oxygen bridged ring is achieved in a two-step combined yield of 72% by using Lewis acid induced intra- molecular Prins cyclization.

Result

Key words: guaiane, chiral oxygen bridge seven-membered ring, Prins reaction

Cite this article

Minshou Wang, Hongbin Zhang. Synthesis of Framework Structure of Guaiane[J]. Chinese Journal of Organic Chemistry, 2021, 41(4): 1739-1743.

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Fig. & Tab. 5

References 19

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Entry	Condition^b^,^c	Substrate^d	Tempreature/℃	Result
1	LiHMDS, ZnCl₂, N₂	Dioxinone	–78	No reaction
2	KHMDS, ZnCl₂, N₂	Dioxinone	–78	No reaction
3	NaHMDS, BF₃?OEt₂, N₂	Dioxinone	–78	No reaction
4	LiHMDS, BF₃?OEt₂, N₂	Dioxinone	–78	No reaction
5	KHMDS, BF₃?OEt₂, N₂	Dioxinone	–78	No reaction

Entry	Condition^b^,^c	Substrate^d	Tempreature/℃	Result
1	LiHMDS, ZnCl₂, N₂	Dioxinone	–78	No reaction
2	KHMDS, ZnCl₂, N₂	Dioxinone	–78	No reaction
3	NaHMDS, BF₃?OEt₂, N₂	Dioxinone	–78	No reaction
4	LiHMDS, BF₃?OEt₂, N₂	Dioxinone	–78	No reaction
5	KHMDS, BF₃?OEt₂, N₂	Dioxinone	–78	No reaction

Guaiane的骨架结构合成研究

Synthesis of Framework Structure of Guaiane

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Fig. & Tab. 5

References 19

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