自由基多烯环化反应在天然产物全合成中的应用

doi:10.6023/cjoc202204044

有机化学 ›› 2022, Vol. 42 ›› Issue (9): 2703-2714.DOI: 10.6023/cjoc202204044 上一篇下一篇

综述与进展

自由基多烯环化反应在天然产物全合成中的应用

姚良才^a, 桂敬汉^b^,^*()

a 上海师范大学化学与材料科学学院上海 200233
b 中国科学院上海有机化学研究所中国科学院天然产物有机合成化学重点实验室上海 200032

收稿日期:2022-04-17 修回日期:2022-06-02 发布日期:2022-06-16
通讯作者: 桂敬汉
基金资助:
国家重点研发计划(2021YFF0502400); 国家自然科学基金(22122112); 国家自然科学基金(21871289); 上海市科学技术委员会(21ZR1476400); 上海市扬帆计划(21YF1456400); 国家中医药管理局多学科交叉创新团队(ZYYCXTD-202004)

Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis

Liangcai Yao^a, Jinghan Gui^b()

a College of Chemistry and Materials Science, Shanghai Normal University, Shanghai 200233
b CAS Key Laboratory of Synthetic Chemistry of Natural Substances, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, Shanghai 200032

Received:2022-04-17 Revised:2022-06-02 Published:2022-06-16
Contact: Jinghan Gui
Supported by:
National Key Research and Development Program of China(2021YFF0502400); National Natural Science Foundation of China(22122112); National Natural Science Foundation of China(21871289); Science and Technology Commission of Shanghai Municipality(21ZR1476400); Shanghai Sailing Program(21YF1456400); Innovation Team and Talents Cultivation Program of National Administration of Traditional Chinese Medicine(ZYYCXTD-202004)

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摘要/Abstract

多环化合物普遍存在于天然产物、合成药物、农药化学品和精细化学品中, 具有广泛的生物活性, 因此如何高效合成多环化合物是有机合成的一个重要研究方向. 近年来, 多烯烃的自由基串联环化反应越来越成为构建多环骨架的一种可靠、简便途径, 然而目前有关自由基串联环化方面的研究论文特别是近年来发展的环氧均裂开环引发自由基多烯环化反应并未被总结归纳. 因此主要综述了自由基多烯环化反应的引发方法及其在多环天然产物合成中的应用, 将着重介绍环氧多烯在Ti(III)作用下的自由基多烯串联环化反应.

关键词: 多环骨架, 环氧多烯, 自由基, 串联环化, 天然产物合成

Polycyclic compounds, which exist widely in natural products, synthetic drugs, agrochemicals, fine chemicals, etc. have a wide range of biological activities. Therefore, efficient synthesis of polycyclic compounds is an important research direction in organic synthesis. In recent years, free radical cascade cyclization of polyenes has increasingly become a reliable and concise way to construct polycyclic skeletons. However, the research papers on free radical cascade cyclization, especially those initiated by the homolysis of epoxides, have not been summarized. Therefore, this paper mainly reviews the initiation methods of free radical polyene cascade cyclization and its application in the synthesis of polycyclic natural products, with an emphasis on the Ti(III)-mediated free radical cascade cyclization of polyene epoxides.

Key words: polycyclic skeleton, polyene epoxide, free radical, cascade cyclization, natural product synthesis

引用此文

姚良才, 桂敬汉. 自由基多烯环化反应在天然产物全合成中的应用[J]. 有机化学, 2022, 42(9): 2703-2714.

Liangcai Yao, Jinghan Gui. Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis[J]. Chinese Journal of Organic Chemistry, 2022, 42(9): 2703-2714.

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图/表 17

图式1. 角鲨烯生源反应途径

Scheme 1. Biogenetic reaction pathways of squalene

图式2. Yamamoto组不对称多烯串联环化研究

Scheme 2. Studies of the asymmetric polyene cyclization by Yamamoto group

图式3. Corey组不对称串联环化研究

Scheme 3. Studies of the asymmetric polyene cyclization by Corey group

图式4. Corey组(+)-dysideapalaunic acid全合成

Scheme 4. Total synthesis of (+)-dysideapalaunic acid by Corey group

图式5. Corey组scalarenedial全合成

Scheme 5. Total synthesis of scalarenedial by Corey group

图式6. 三种自由基多烯环化反应引发方式

Scheme 6. Three initiation methods of free radical polyene cascade cyclization

图式7. Trotta组oridamycins A和B全合成

Scheme 7. Total synthesis of oridamycins A and B by Trotta group

图式8. Yang组雷公藤素家族天然产物不对称全合成

Scheme 8. Asymmetric total synthesis of triptolide family natural products by Yang group

图式9. Curran组hirsutene全合成

Scheme 9. Total synthesis of hirsutene by Curran group

图式10. Pattenden组基于锡氢还原启动的自由基串联环化研究

Scheme 10. Pattenden group's studies of free radical cascade cyclization initiated by Sn-H

图式11. Nugent组基于Ti(III)氧化启动的自由基串联环化研究

Scheme 11. Studies of Ti(III)-initiated free radical cascade cyclization by Nugent group

图式12. Takahashi组smenospondiol全合成

Scheme 12. Total synthesis of smenospondiol by Takahashi group

图式13. Oltra组furanospongian diterpenes A和B全合成

Scheme 13. Total synthesis of furanospongian diterpenes A and B by Oltra group

图式14. Cardenas组barekoxide和laukarlaol全合成

Scheme 14. Total synthesis of barekoxide and laukarlaol by Cardenas group

图式15. Barrero组(-)-valpara-2,15-diene全合成

Scheme 15. Total synthesis of (-)-valpara-2,15-diene by Barrero group

图式16. Maimone组berkeleyone A全合成

Scheme 16. Total synthesis of berkeleyone A by Maimone group

图式17. Xu组walsucochin B和walsucochinoids M和N全合成

Scheme 17. Total synthesis of walsucochin B and walsucochinoids M and N by Xu group

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自由基多烯环化反应在天然产物全合成中的应用

Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis

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