Guaiane的骨架结构合成研究

doi:10.6023/cjoc202009010

有机化学 ›› 2021, Vol. 41 ›› Issue (4): 1739-1743.DOI: 10.6023/cjoc202009010 上一篇下一篇

研究简报

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

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摘要/Abstract

报道了一种基于Prins环化反应合成手性五元并七元氧桥环结构的方法, 为愈创木烷型倍半萜类天然产物骨架结构的合成提供了一种新思路. 该合成工作是以dioxinone为基础, 利用路易斯酸诱导发生分子内的Prins环化反应, 以两步72%的联合收率实现了手性[5,7]并环氧桥环的合成.

关键词: 愈创木烷, 手性氧桥七元环, Prins反应

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

引用此文

王敏寿, 张洪彬. Guaiane的骨架结构合成研究[J]. 有机化学, 2021, 41(4): 1739-1743.

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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图/表 5

图1. 代表性愈创木烷型倍半萜类天然产物

Figure 1. Representative guaianes-type sesquiterpenoid natural products

图式1. 合成5,7并环的代表性例子和本研究组的工作

Scheme 1. Representative examples of synthesizing 5,7-fused ring and our work

图式2. 目标化合物14的合成路线

Scheme 2. Synthetic route of target compound 14

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

表1. 化合物17的合成尝试a

Table 1. Attempt to synthesize compound 17

图式3. 目标化合物20的合成路线

Scheme 3. Synthetic route of target compound 20

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Guaiane的骨架结构合成研究

Synthesis of Framework Structure of Guaiane

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