Application of the Radical Polyene Cyclization Reaction in Natural Product Synthesis

doi:10.6023/cjoc202204044

Chinese Journal of Organic Chemistry ›› 2022, Vol. 42 ›› Issue (9): 2703-2714.DOI: 10.6023/cjoc202204044 Previous Articles Next Articles

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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

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)

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

Cite this article

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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Fig. & Tab. 17

Scheme 1. Biogenetic reaction pathways of squalene

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

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

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

Scheme 5. Total synthesis of scalarenedial by Corey group

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

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

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

Scheme 9. Total synthesis of hirsutene by Curran group

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

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

Scheme 12. Total synthesis of smenospondiol by Takahashi group

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

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

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

Scheme 16. Total synthesis of berkeleyone A by Maimone group

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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