Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction

doi:10.6023/A25040131

Acta Chimica Sinica ›› 2025, Vol. 83 ›› Issue (11): 1424-1434.DOI: 10.6023/A25040131 Previous Articles Next Articles

Review

基于自由基介导Formal Diels-Alder反应的复杂天然产物全合成

黄俊^*(), 尹蓉, 曹婷婷

南华大学化学化工学院湖南衡阳 421001

投稿日期:2025-04-24 发布日期:2025-05-22
通讯作者: 黄俊

作者简介:

黄俊, 教授, 博士生导师. 2010年7月毕业于中国农业大学理学院化学系, 获得理学学士学位; 2015年7月于北京大学获得博士学位; 2015年8月至2016年9月于美国纽约州立大学奥尔巴尼分校进行博士后研究; 2016年10月至2021年9月就职于北京大学深圳研究生院; 2021年10月至今, 就职于南华大学化学化工学院. 主要从事天然产物全合成及合成方法学研究.

尹蓉, 2022年7月于湖南理工学院获得理学学士学位, 同年进入南华大学攻读硕士学位. 指导教师为黄俊教授, 研究方向为天然小分子药物全合成. 目前已完成鬼臼毒素类家族分子的结构多样性全合成研究.

曹婷婷, 2017年7月于湖北大学获得理学学士学位; 2022年7月于北京大学获得博士学位; 目前于英国格拉斯哥大学进行博士后研究. 研究方向为人工智能和自动化化学合成.

基金资助:
项目受国家自然科学基金(22371117); 湖南省科技创新计划(2022RC1106)

Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction

Huang Jun^*(), Yin Rong, Cao Tingting

School of Chemistry and Chemical Engineering, University of South China, Hengyang, Hunan 421001

Received:2025-04-24 Published:2025-05-22
Contact: Huang Jun
Supported by:
National Natural Science Foundation of China(22371117); Science and Technology Innovation Program of Hunan Province(2022RC1106)

In recent years, the radical-mediated formal Diels-Alder reaction of dienophiles and dienes under mild conditions has provided a novel approach for the stereoselective construction of six-membered ring skeleton. This review offers a concise overview of the application of radical-mediated formal Diels-Alder reactions in the total synthesis of bioactive complex natural products. It mainly includes three types of reaction pathways: (1) the radical cation-mediated formal Diels-Alder reaction, (2) the single-electron-transfer-initiated formal Diels-Alder reaction, and the diradical-involved formal Diels-Alder reaction, which enable the stereoselective generation of target ring systems.

Key words: radical cation, diradical, formal-Diels-Alder reaction, [4＋2]-cycloaddition reaction, total synthesis of natural products

Cite this article

Huang Jun, Yin Rong, Cao Tingting. Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction[J]. Acta Chimica Sinica, 2025, 83(11): 1424-1434.

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Fig. & Tab. 12

Scheme 1. Applications of the Diels-Alder reaction in the total synthesis of representative natural products

Scheme 2. Reaction types of radical-meidated formal Diels-Alder reaction: (a) cation radical; (b) single electron transfer (SET); (c) diradical

Scheme 3. Cation radical-mediated formal Diels-Alder reaction

Scheme 4. Total synthesis of (－)-β-Selinene

Scheme 5. Total synthesis of Kingianins A, D and F

Scheme 6. Total synthesis of Kingianin A

Scheme 7. Total synthesis of Brosimones A and B

Scheme 8. Total synthesis of aryltetralin ether lignans

Scheme 9. Proposed biosynthetic pathway of 1,4-benzodioxane lignans

Scheme 10. Total synthesis of (±)-Aiphanol and (±)-nitidanin

Scheme 11. Total synthesis of Brevitaxin

Scheme 12. Total synthesis of Lucidumone

References 83

[1]	(a) Atanasov A. G.; Zotchev S. B.; Dirsch V. M.; Supuran C. T. Nat. Rev. Drug Discover. 2021, 20, 200.
	(b) Newman D. J.; Cragg G. M. J. Nat. Prod. 2020, 83, 770.
[2]	(a) Ylijoki K. E. O.; Stryker J. M. Chem. Rev. 2013, 113, 2244.
	(b) Doerksen R. S.; Hodík T.; Hu G.; Huynh N. O.; Shuler W. G.; Krische M. J. Chem. Re.. 2021, 121, 4045.
	(c) Hu Y.-J.; Li L.-X.; Han J.-C.; Min L.; Li C.-C. Chem. Re.. 2020, 120, 5910.
	(d) Min L.; Liu X.; Li C.-C. Acc. Chem. Re.. 2020, 53, 703.
	(e) Nicolaou K. C.; Snyder S. A.; Montagnon T.; Vassilikogiannakis G. Angew. Chem., Int. Ed. 2002, 41, 1668.
[3]	Diels O.; Alder K. Liebigs Ann. Che.. 1928, 460, 98.
[4]	Sustmann R. Pure Appl. Che.. 1974, 40, 569.
[5]	Woodward R. B.; Hoffmann R. Angew. Chem., Int. Ed. 1969, 8, 781.
[6]	Png Z. M.; Zeng H. N.; Ye Q. Chem. - Asian J. 2017, 12, 2142.
[7]	(a) Corey E. J. Angew. Chem., Int. Ed. 2002, 41, 1650.
	(b) Jiang X.; Wang R. Chem. Re.. 2013, 113, 5515.
	(c) Brieger G.; Bennett J. N. Chem. Re.. 1980, 80, 63.
	(d) Eschenbrenner-Lux V.; Kumar K.; Waldmann H. Angew. Chem., Int. Ed. 2014, 53, 11146.
[8]	(a) Danishefsky S. Acc. Chem. Re.. 1981, 14, 400.
	(b) Savard J.; Brassard P. Tetrahedron Let.. 1979, 20, 4911.
	(c) Huang Y. A.; Unni K.; Thadani A. N.; Rawal V. H. Natur. 2003, 424, 146.
	(d) Lv J.; Zhong X.; Cheng J.-P.; Luo S. Acta Chim. Sinic. 2012, 70, 1518 (in Chinese).
	(吕健, 钟兴仁, 程津培, 罗三中, 化学学报, 2012, 70, 1518.)
	(e) Burford R. J.; Li B.; Vasiiu M.; Dixon D. A.; Liu S.-Y. Angew. Chem., Int. Ed. 2015, 54, 7823.
	(f) Suzuki S.; Segawa Y.; Itami K.; Yamaguchi J. Nat. Che.. 2015, 7, 227.
	(g) Zhou Y.; Zhou Z.; Du W.; Chen Y. Acta Chim. Sinic. 2018, 76, 382 (in Chinese).
	(周远春, 周志, 杜玮, 陈应春, 化学学报, 2018, 76, 382.)
	(h) Cai Q. Chin. J. Che.. 2019, 37, 946.
	(i) Wang Z.-S.; Bennett S. H.; Kicin B.; Jing C.; Pradeilles J. A.; Thai K.; Smith J. R.; Bacoş P. D.; Fasano V.; Saunders C. M.; Aggarwal V. K. J. Am. Chem. So.. 2023, 145, 14124.
	(j) Si X.-G.; Zhang Z.-M.; Zheng C.-G.; Li Z.-T.; Cai Q. Angew. Chem., Int. Ed. 2020, 59, 18412.
	(k) Lu Y.; Xu M.-M.; Zhang Z.-M.; Zhang J.-L.; Cai Q. Angew. Chem., Int. Ed. 2021, 60, 26610.
	(l) Du Y.-B.; Lu Q.-T.; Cui Y.-S.; Wu K.-W.; Wang Y.; Zhang Y.-Z.; Zhao Z.; Hou J.-L.; Cai Q. Angew. Chem., Int. Ed. 2025, 64, e202421060.
	(m) He Q.; Xu Z.; Fang H.; Liu S.; Lu X.; Hong X.; Fu Y.; Liu G.; Huang Z. Angew. Chem., Int. Ed. 2025, 64, e202425232.
	(n) Zhang F.; Wang Yu.; Tan Z.; Liu Y.; Song L.; Feng X. Chin. Chem. Lett. 2025, 36, 110581.
	(o) Ding X.; Deng W. Chin. J. Org. Che.. 2020, 40, 3976 (in Chinese).
	(丁祥峰, 邓卫平, 有机化学, 2020, 40, 3976.)
[9]	(a) Ma D.; Liu Y.; Wang Z. Angew. Chem., Int. Ed. 2017, 56, 7886.
	(b) Huang J. H.; Gu Y.; Guo K.; Zhu L.; Lan Y.; Gong J.; Yang Z. Angew. Chem., Int. Ed. 2017, 56, 7890.
	(c) Feng J.; Lei X.; Guo Z.; Tang Y. Angew. Chem., Int. Ed. 2017, 56, 7895.
	(d) Long X.; Huang Y.; Long Y.; Deng J. Org. Chem. Front. 2018, 5, 1152.
	(e) Yuan C.; Du B.; Yang L.; Liu B. J. Am. Chem. Soc. 2013, 135, 9291.
	(f) Fu S.; Liu B. Chin. J. Chem. 2022, 40, 407.
	(g) Yu M.; Danishefsky S. J. J. Am. Chem. Soc. 2008, 130, 2783.
	(h) Smith B. R.; Njardarson J. T. Org. Biomol. Che.. 2018, 16, 4210.
	(i) Gong J.; Lin G.; Sun W.; Li C.-C.; Yang Z. J. Am. Chem. So.. 2010, 132, 16745.
	(j) Peng F.; Danishefsky S. J. J. Am. Chem. So.. 2012, 134, 18860.
	(k) Lu P.; Gu Z.; Zakarian A. J. Am. Chem. So.. 2013, 135, 14552.
	(l) Zheng C; Dubovyk I.; Lazarski K. E.; Thomson R. J. J. Am. Chem. Soc. 2014, 136, 17750.
	(m) Min L.; Han J.-C.; Zhang W.; Gu C.-C.; Zou Y.-P.; Li C.-C. Chem. Rev. 2023, 123, 4934.
	(n) Tessier G.; Barriault L. Org. Prep. Proced. In.. 2007, 39, 311.
	(o) Huters A. D.; Garg N. K. Chem. Eur. J. 2010, 16, 8586.
	(p) Draghici C.; Njardarson J. T. Tetrahedro. 2015, 71, 3775.
	(q) Betkekar V. V.; Kaliappan K. P. Tetrahedron Lett. 2018, 59, 2485.
	(r) Yu X.; Xiao L.; Wang Z.; Luo T. J. Am. Chem. Soc. 2019, 141, 3440.
[10]	(a) Funel J.-A.; Abele S. Angew. Chem., Int. Ed. 2013, 52, 3822.
	(b) Liu B.; Fu S.; Zhou C. Nat. Prod. Rep. 2020, 37, 1627.
	(c) Yang B.; Hou M.; Gao S. Acc. Chem. Res. 2025, 58, 1308.
	(d) Xiong X.; Chen H. Chin. J. Org. Che.. 2013, 33, 1437 (in Chinese).
	(熊兴泉, 陈会新, 有机化学, 2013, 33, 1437.)
[11]	(a) Fischer H.; Radom L. Angew. Chem., Int. Ed. 2001, 40, 1340.
	(b) Roberts B. P. Chem. Soc. Rev. 1999, 28, 25.
[12]	Parsons A. F. An Introduction to Free Radical Chemistr., Blackwell Science Ltd, Oxford, 2000.
[13]	Schenck G. O.; Mannsfeld S.-P.; Schomburg G.; Krauch C. H. Z. Narurfirsc. 1964, 198, 18.
[14]	Bawn C. E. H.; Bell F. A.; Ledwith A. Chem. Commun. 1968, 599.
[15]	Bauld N. L.; Bellville D. J.; Harirchian B.; Lorenz K. T.; Pabon R. A.; Reynolds D. W.; Wirth D. D.; Chiou H. S.; Marsh B. K. Acc. Chem. Re.. 1987, 20, 371.
[16]	Bauld N. L. Tetrahedro. 1989, 45, 5307.
[17]	(a) Haberl U.; Wiest O.; Steckhan E. J. Am. Chem. Soc. 1999, 121, 6730.
	(b) Pérez-Ruiz R.; Domingo L. R.; Jiménez M. C.; Miranda M. A. Org. Lett. 2011, 13, 5116.
	(c) Tan J. S. J.; Hirvonen V.; Paton R. S. Org. Let.. 2018, 20, 2821.
[18]	Studer A.; Curran D. P. Nat. Che.. 2014, 6, 765.
[19]	(a) Wright J. S.; Johnson E. R.; DiLabio G. A. J. Am. Chem. Soc. 2001, 123, 1173.
	(b) Hioe J.; Zipse C. Org. Biomol. Che.. 2010, 8, 3609.
	(c) Chabuka B. K.; Alabugin I. V. J. Am. Chem. So.. 2023, 145, 19354.
[20]	(a) Okada Y.; Chiba K. Chem. Re.. 2018, 118, 4592.
	(b) Sicignano Marina.; Rodríguez R.I.; Alemán J. Eur. J. Org. Che.. 2021, 3303.
[21]	(a) Lin S.; Ischay M. A.; Fry C. G.; Yoon T. P. J. Am. Chem. So.. 2011, 133, 19350.
	(b) Farney E. P.; Chapman S. J.; Swords W. B.; Torelli M. D.; Hamers R. J.; Yoon T. P. J. Am. Chem. So.. 2019, 141, 6385.
[22]	(a) Stevenson S. M.; Shores M. P.; Ferreira E. M. Angew. Chem., Int. Ed. 2015, 54, 6506.
	(b) Stevenson S. M.; Higgins R. F.; Shores M. P.; Ferreira E. M. Chem. Sc.. 2017, 8, 654.
[23]	Higgins R. F.; Fatur S. M.; Shepard S. G.; Stevenson S. M.; Boston D. J.; Ferreira E. M.; Damrauer N. H.; Rappé A. K.; Shores M. P. J. Am. Chem. So.. 2016, 138, 5451.
[24]	Alpers D.; Gallhof M.; Stark C. B. W.; Brasholz M. Chem. Commu.. 2016, 52, 1025.
[25]	Wang L.; Wu F.; Chen J.; Nicewicz D. A.; Huang Y. Angew. Chem., Int. Ed. 2017, 56, 6896.
[26]	Zhao Y.; Antonietti M. Angew. Chem., Int. Ed. 2017, 56, 9336.
[27]	Tanaka K.; Kishimoto M.; Sukekawa M.; Hoshino Y.; Honda K. Tetrahedron Lett. 2018, 59, 3361.
[28]	Zhang G.; Lin Y.; Luo X.; Hu X.; Chen C.; Lei A. Nat. Commu.. 2018, 9, 1225.
[29]	Nakayama K.; Maeta N.; Horiguchi G.; Kamiya H.; Okada Y. Org. Lett. 2019, 21, 2246.
[30]	Huber N.; Li R.; Ferguson C. T. J.; Gehrig D. W.; Ramanan C.; Blom P. W. M.; Landfester K.; Zhang K. A. I. Catal. Sci. Technol. 2020, 10, 2092.
[31]	(a) Tanaka K.; Kishimoto M.; Tanaka Y.; Kamiyama Y.; Asada Y.; Sukekawa M.; Ohtsuka N.; Suzuki T.; Momiyama N.; Honda K.; Hoshino Y. J. Org. Che.. 2022, 87, 3319.
	(b) Chen X. Y.; Kuang X.; Wu Y.; Zhou J.; Wang P. Chin. J. Chem. 2023, 41, 1979.
[32]	Jang Y. J.; An H.; Choi S.; Hong J.; Lee S. H.; Ahn K.-H.; You Y.; Kang E. J. Org. Let.. 2022, 24, 4479.
[33]	Brambilla E.; Moretti E.; Magni M.; Abbiati G.; Pirovano V. Chem. Commu.. 2023, 59, 3281.
[34]	Ohmura S.; Katagiri K.; Kato H.; Horibe T.; Miyakawa S.; Hasegawa J.; Ishihara K. J. Am. Chem. So.. 2023, 145, 15054.
[35]	Jang I.; Kim H. Y.; Oh K. Org. Lett. 2024, 26, 4008.
[36]	Guo L.; Chu R.; Hao X.; Lei Y.; Li H.; Ma D.; Wang G.; Tung C.-H.; Wang Y. Nat. Commu.. 2024, 15, 979.
[37]	Hisada T.; Maeda K.; Yamashita Y.; Kobayashi S. Org. Lett. 2025, 27, 4366.
[38]	Yang Y.; Liu Q.; Zhang L.; Yu H.; Dang Z. Organometallic. 2017, 36, 687.
[39]	Valentine D.; Turro N. J., Jr.; Hammond G. S. J. Am. Chem. So.. 1964, 86, 5202.
[40]	(a) Pabon R. A.; Bellville D. J.; Bauld N. L. J. Am. Chem. So.. 1983, 105, 5158.
	(b) Harirchian B.; Bauld N. L. J. Am. Chem. So.. 1989, 111, 1826.
[41]	(a) Glasby J. S. Encyclopedia of the Terpenoid., John Wiley & Sons, Chichester, New York, 1982, p. 2646.
	(b) Ruzicka L.; Wind A. H. Helv. Chim. Act. 1931, 14, 1132.
	(c) Stevens R. Chem. Re.. 1967, 67, 19.
	(d) Shigemitsu N.; Kitazawa Y. Bull. Brewing Sc.. (Jpn) 1962, 8, 23.
[42]	Leverrier A.; Tran Huu Dau M. E.; Retailleau P.; Awang K.; Guéritte F.; Litaudon M. Org. Let.. 2010, 12, 3638.
[43]	(a) Nicolaou K. C.; Petasis N. A.; Zipkin R. E.; Uenishi J. J. Am. Chem. Soc. 1982, 104, 5555.
	(b) Banfield J. E.; Black D.; Johns S. R.; Willing R. I. Aust. J. Che.. 1982, 35, 2247.
[44]	Drew S. L.; Lawrence A. L.; Sherburn M. S. Angew. Chem., Int. Ed. 2013, 52, 4221.
[45]	Matovic N. J.; Hayes P. Y.; Penman K.; Lehmann R. P.; De Voss J. J. J. Org. Che.. 2011, 76, 4467.
[46]	Huisgen R.; Dahmen A.; Huber H. J. Am. Chem. So.. 1967, 89, 7130.
[47]	Drew S. L.; Lawrence A. L.; Sherburn M. S. Chem. Sci. 2015, 6, 3886.
[48]	Lim H. N.; Parker K. A. Org. Let.. 2013, 15, 398.
[49]	Parker K. A.; Wang Z. Org. Lett. 2006, 8, 3553.
[50]	Messana I.; Ferrari F. Tetrahedro. 1988, 44, 6693.
[51]	Messana I.; Ferrari F.; de Mello J. F.; do Carmo Mesquita de Araujo M. Heterocycle. 1989, 29, 683.
[52]	(a) Fukutani T.; Umeda N.; Hirano K.; Satoh T.; Miura M. Chem. Commu.. 2009, 5141.
	(b) Nakao Y.; Morita E.; Idei H.; Hiyama T. J. Am. Chem. Soc. 2011, 133, 3264.
	(c) Ozawa T.; Kurahashi T.; Matsubara S. Org. Lett. 2011, 13, 5390.
	(d) Stang E. M.; White M. C. J. Am. Chem. So.. 2011, 133, 14892.
	(e) Ohashi M.; Takeda I.; Ikawa M.; Ogoshi S. J. Am. Chem. So.. 2011, 133, 18018.
	(f) Dong S.; Qin T.; Hamel E.; Beutler J. A.; Porco J. A. Jr. J. Am. Chem. So.. 2012, 134, 19782.
[53]	Qi C.; Cong H.; Cahill K. J.; Müller P.; Johnson R. P.; Porco J. A. Jr. Angew. Chem., Int. Ed. 2013, 52, 1.
[54]	(a) Cong H.; Becker C. F.; Elliott S. J.; Grinstaff M. W.; Porco J. A. Jr. J. Am. Chem. So.. 2010, 132, 7514.
	(b) Cong H.; Porco J. A. Jr. ACS Catal. 2012, 2, 65.
	(c) Cong H.; Porco J. A. Jr. Org. Lett. 2012, 14, 2516.
[55]	(a) Halton B.; Russell S. G. G. Aust. J. Che.. 1992, 45, 1069.
	(b) Jigami T.; Takimiya K.; Otsubo T. J. Org. Che.. 1998, 63, 8865.
	(c) Schumacher R. F.; Rosario A. R.; Souza A. C. G.; Menes P. H.; Zeni G. Org. Let.. 2010, 12, 1952.
[56]	Nomura T. Yakugaku Zassh. 2001, 121, 535.
[57]	Yu X.; Che Z.; Xu H. Chem. Eur. J. 2017, 23, 4467.
[58]	(a) Wang B. G.; Ebel R.; Nugroho B. W.; Prijono D.; Frank W.; Steube K. G.; Hao X. J.; Proksch P. J. Nat. Pro.. 2001, 64, 1521.
	(b) Wang B. G.; Ebel R.; Wang C. Y.; Wray V.; Proksch P. Tetrahedron Let.. 2002, 43, 5783.
	(c) Zhang Z.; Guo D.; Zheng J.; Koike K.; Jia Z.; Nikaido T. Heterocycle. 2000, 53, 675.
	(d) Nose M.; Bernards M. A.; Furlan M.; Zajicek J.; Eberhardt T. L.; Lewis N. G. Phytochemistr. 1995, 39, 71.
	(e) Shang S. Z.; Chen H.; Liang C. Q.; Gao Z. H.; Du X.; Wang R. R.; Shi Y. M.; Zheng Y. T.; Xiao W. L.; Sun H. D. Arch. Pharmacal Re.. 2013, 36, 1223.
	(f) Miyata R.; Sahlan M.; Ishikawa Y.; Hashimoto H.; Honda S.; Kumazawa S. J. Nat. Pro.. 2020, 83, 1356.
[59]	(a) Sellars J. D.; Steel P. G. Eur. J. Org. Chem. 2007, 3815.
	(b) Zhang X.; Rakesh K. P.; Shantharam C. S.; Manukumar H. M.; Asiri A. M.; Marwani H. M.; Qin H. L. Bioorg. Med. Che.. 2018, 26, 340.
[60]	Xiang J.-C.; Wang Q.; Zhu J. Angew. Chem., Int. Ed. 2020, 59, 21195.
[61]	(a) Kim T.; Mirafzal G. A.; Liu J.; Bauld N. L. J. Am. Chem. Soc. 1993, 115, 7653.
	(b) Schepp N. P.; Shukla D.; Sarker H.; Bauld N. L.; Johnston L. J. J. Am. Chem. So.. 1997, 119, 10325.
[62]	(a) Beckwith A. L. J.; Schiesser C. H. Tetrahedro. 1985, 41, 3925.
	(b) Spellmeyer D. C.; Houk K. N. J. Org. Che.. 1987, 52, 959.
	(c) RajnBabu T. V. Acc. Chem. Res. 1991, 24, 139.
[63]	Pilkington L. I.; Barker D. Nat. Prod. Re.. 2015, 32, 1369.
[64]	Salae A.-W.; Boonnak N. Tetrahedron Lett. 2013, 54, 1356.
[65]	Aoyagi Y.; Takahashi Y.; Satake Y.; Fukaya H.; Takeya K.; Aiyama R.; Matsuzaki T.; Hashimoto S.; Shiina T.; Kurihara T. Tetrahedron Let.. 2005, 46, 7885.
[66]	Xu G.; Yang X. W.; Wu C. Y.; Li X. N.; Su J.; Deng X.; Li Y.; Qin H. B.; Yang L. X.; Zhao Q. S. Chem. Commun. 2012, 48, 4438.
[67]	Ray A. B.; Chattopadhyay S. K.; Konno C.; Hikino H. Tetrahedron Let.. 1980, 21, 4477.
[68]	Ray A. B.; Chattopadhyay S. K.; Konno C.; Hikino H. Heterocycle. 1982, 19, 19.
[69]	Hasegawa T.; Fukuyama Y.; Koshino K.; Nakagawa K.; Tori M.; Asakawa Y. Chem. Lett. 1987, 16, 329.
[70]	Kuboki A.; Yamamoto T.; Ohira S. Chem. Lett. 2003, 32, 420.
[71]	Kuboki A.; Yamamoto T.; Taira M.; Arishige T.; Ohira S. Tetrahedron Lett. 2007, 48, 771.
[72]	Kuboki A.; Yamamoto T.; Taira M.; Arishige T.; Konishi R.; Hamabata M.; Shirahama M.; Hiramatsu T.; Kuyama K.; Ohira S. Tetrahedron Lett. 2008, 49, 2558.
[73]	Arslanian R. L. D.; Bailey T.; Kent M. C.; Richheimer S. L.; Thornburg K. R.; Timmons D. W.; Zheng Q. Y. J. Nat. Prod. 1995, 58, 583.
[74]	(a) Chen H.-L.; Lin K.-W.; Gan K.-H.; Wang J.-P.; Won S.-J.; Lin C.-N. Fitoterapi. 2011, 82, 219.
	(b) Liang J.-Y.; Huang K.-S.; Guanatilaka A. A. L.; Yang L. Phytochemistr. 1998, 47, 69.
[75]	Simmons E. M.; Sarpong R. Nat. Prod. Rep. 2009, 26, 1195.
[76]	Lu Y.; Cao T.; Li K.; Lin Y.-W.; Zhu L.; Huang J. Org. Lett. 2024, 26, 5237.
[77]	(a) Rich P. R. Biochim. Biophys. Act. 1981, 637, 28.
	(b) Warren J. J.; Tronic T. A.; Mayer J. M. Chem. Re.. 2010, 110, 6961.
[78]	Yan Y.-M.; Zhang H.-X.; Liu H.; Wang Y.; Wu J.-B.; Li Y.-P.; Cheng Y.-X. Org. Lett. 2019, 21, 8523.
[79]	(a) Ma S.; Li Z.; Yu P.; Shi H.; Yang H.; Yi J.; Zhang Z.; Duan X.; Xie X.; She X. Org. Lett. 2022, 24, 5541.
	(b) Huang G.; Kouklovsky C.; de la Torre A. J. Am. Chem. So.. 2022, 144, 17803.
	(c) Liao X.-Z.; Wang R.; Wang X.; Li G. Nat. Commu.. 2024, 15, 2647.
[80]	Xu Z.; Peng W.; Huang J.; Shen J.; Guo J.-J.; Hu A. Nat. Commun. 2024, 15, 9748.
[81]	Jackl M. K.; Legnani L.; Morandi B.; Bode J. W. Org. Let.. 2017, 19, 4696.
[82]	(a) Watanabe K. J. Nat. Me.. 2021, 75, 434.
	(b) Ghattas W.; Mahy J.-P.; Réglier M.; Simaan A. J. ChemBioChe. 2021, 22, 443.
	(c) Oikawa H.; Tokiwano T. Nat. Prod. Re.. 2004, 21, 321.
[83]	(a) Horibe T.; Ohmura S.; Ishihara K. J. Am. Chem. So.. 2019, 141, 1877.
	(b) Das S.; Zhu C.; Demirbas D.; Bill E.; De C. K.; List B. Scienc. 2023, 379, 494.
	(c) Blum T. R.; Miller Z. D.; Bates D. M.; Guzei I. A.; Yoon T. P. Scienc. 2016, 354, 1391.

基于自由基介导Formal Diels-Alder反应的复杂天然产物全合成

Total Synthesis of Complex Natural Products Via Radical-Mediated Formal Diels-Alder Reaction

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[1]	Jie Yang, Lin Ling, Yuxue Li, Long Lu. Density Functional Theory Study on Thermal Decomposition Mechanisms of Ammonium Perchlorate [J]. Acta Chimica Sinica, 2023, 81(4): 328-337.
[2]	Wang Yinghui, Jie Jialong, Zhao Hongmei, Bai Yu, Qin Peixuan, Song Di. Deprotonation of Guanine Radical Cation in G-Quadruplex: A Combined Experimental and Theoretical Study [J]. Acta Chim. Sinica, 2018, 76(6): 475-482.
[3]	Gao Xiao-Fei, He Peng, Chen Huanwen. Study on the Interaction Between Water Radical Cations and Bis(2-hydroxyethyl) Disulfide at Ambient Temperature and Pressure Using Mass Spectrometry [J]. Acta Chim. Sinica, 2018, 76(10): 802-806.
[4]	Li Zhuo, Du Xiaofeng, Ma Nana, Sun Shiling, Qiu Yongqing. Theoretical Study on NLO Properties of TTF^+·-π Conjugated Bridge-verdazyl Cation Diradicals [J]. Acta Chimica Sinica, 2012, 70(02): 107-113.
[5]	LIU Hai-Bo, CHOU Yong-Qing, SUN Shi-Ling, LIU Chun-Guang, SUN Xiao-Na. DFT Study on Nonlinear Optical Properties of Open and Closed Shell Systems of TCNQ Involving Different Conjugation Bridges [J]. Acta Chimica Sinica, 2010, 68(24): 2509-2515.