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One-Step Semisynthesis Method of Spirocurcasone and Pyracurcasone from Curcusones A and B

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State Key Laboratory of Photochemistry and Plant Resources in West China, Kunming Institute of Botany, Chinese Academy of Sciences, Kunming 650201, Yunnan People’s Republic of China
University of Chinese Academy of Sciences, Beijing 100049, People’s Republic of China
*E-mail: [email protected] (M.-H. Qiu).
*E-mail: [email protected] (J.-Q. Liu).
*E-mail: [email protected] (H.-B. Qin).
Cite this: Org. Lett. 2014, 16, 8, 2196-2199
Publication Date (Web):April 3, 2014
https://doi.org/10.1021/ol500692j
Copyright © 2014 American Chemical Society
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Abstract

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High contents of curcusones A and B and trace amounts of spirocurcasone exist in the roots of Jatropha curcas. Here, a one-step semisynthesis method of spirocurcasone and pyracurcasone was built, not only resulted an increased yield of spirocurcasone but also produced pyracurcasone, which exhibited greater cytotoxicity compared to curcusones A and B. The plausible mechanism of the formation of pyracurcasone was proposed, and the proposed biogenetic origin for spirocurcasone by Taglialatela-Scafati was confirmed.

Supporting Information

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General experimental procedures, X-ray crystal structure of 1 and 3, detection of intermediate 5 by TLC, absolute configuration of the epoxy group of 6, and spectroscopic data of compounds 18. This material is available free of charge via the Internet at http://pubs.acs.org.

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Cited By


This article is cited by 9 publications.

  1. Luo-Sheng Wan, Li-Dong Shao, Liangbing Fu, Jun Xu, Guo-Lei Zhu, Xing-Rong Peng, Xiao-Nian Li, Yan Li, and Ming-Hua Qiu . One-Step Semisynthesis of a Segetane Diterpenoid from a Jatrophane Precursor via a Diels–Alder Reaction. Organic Letters 2016, 18 (3) , 496-499. DOI: 10.1021/acs.orglett.5b03473.
  2. Andrés Seoane, Noelia Casanova, Noelia Quiñones, José L. Mascareñas, and Moisés Gulías . Rhodium(III)-Catalyzed Dearomatizing (3 + 2) Annulation of 2-Alkenylphenols and Alkynes. Journal of the American Chemical Society 2014, 136 (21) , 7607-7610. DOI: 10.1021/ja5034952.
  3. Toyoharu Kobayashi, Hideki Abe, Hisanaka Ito. Synthetic Studies of Polycyclic Terpenoids Using the Intramolecular Aldol-Type Cyclization Reaction. Journal of Synthetic Organic Chemistry, Japan 2019, 77 (11) , 1086-1095. DOI: 10.5059/yukigoseikyokaishi.77.1086.
  4. Marialuisa Menna, Concetta Imperatore, Alfonso Mangoni, Gerardo Della Sala, Orazio Taglialatela-Scafati. Challenges in the configuration assignment of natural products. A case-selective perspective. Natural Product Reports 2019, 36 (3) , 476-489. DOI: 10.1039/C8NP00053K.
  5. Jie-Qing Liu, Ying Xu, Qin Xiao, Jin-Di Huang, Jun-Jie Ma, Chen-Lei Lian, Mei-Ying Huang, Zhen-bo Du, Cui-Fang Wang. Dimericursones A and B: two unprecedented hexacyclic dimeric diterpenoids from the root barks of Jatropha curcas. Organic & Biomolecular Chemistry 2018, 16 (37) , 8305-8310. DOI: 10.1039/C8OB02082E.
  6. Guillaume Odonne, Emeline Houël, Geneviève Bourdy, Didier Stien. Treating leishmaniasis in Amazonia: A review of ethnomedicinal concepts and pharmaco-chemical analysis of traditional treatments to inspire modern phytotherapies. Journal of Ethnopharmacology 2017, 199, 211-230. DOI: 10.1016/j.jep.2017.01.048.
  7. Dong Chen, Wen-Dan Xu, Hao-Miao Liu, Ming-Ming Li, Yong-Min Yan, Xiao-Nian Li, Yan Li, Yong-Xian Cheng, Hong-Bo Qin. Enantioselective total synthesis of (+)-Lingzhiol via tandem semipinacol rearrangement/Friedel–Crafts type cyclization. Chemical Communications 2016, 52 (55) , 8561-8564. DOI: 10.1039/C6CC03764J.
  8. Laura K. Smith, Ian R. Baxendale. Total syntheses of natural products containing spirocarbocycles. Organic & Biomolecular Chemistry 2015, 13 (39) , 9907-9933. DOI: 10.1039/C5OB01524C.
  9. Xu-Yang Li, Yuan-Feng Yang, Xing-Rong Peng, Ming-Ming Li, Liang-Qun Li, Xu Deng, Hong-Bo Qin, Jie-Qing Liu, Ming-Hua Qiu. ChemInform Abstract: One-Step Semisynthesis Method of Spirocurcasone and Pyracurcasone from Curcusones A and B.. ChemInform 2014, 45 (42) , no-no. DOI: 10.1002/chin.201442243.

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