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Biomimetic Synthesis of Zeylanone and Zeylanone Epoxide by Dimerization of 2-Methyl-1,4-naphthoquinone

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Graduate School for Life and Environmental Sciences, Kyoto Prefectural University, 1-5 Shimogamo Hangi-cho, Sakyo-ku, Kyoto 606-8522, Japan, and Institute for Chemical Research, Kyoto University, Uji, Kyoto 611-0011, Japan
[email protected]
†Kyoto Prefectural University
‡Kyoto University
Cite this: Org. Lett. 2013, 15, 7, 1556–1559
Publication Date (Web):March 25, 2013
https://doi.org/10.1021/ol400335s
Copyright © 2013 American Chemical Society
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Abstract

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A biomimetic synthesis of zeylanone and zeylanone epoxide, which are natural dimeric naphthoquinones, has been accomplished starting from plumbagin, a natural monomeric naphthoquinone. The key features of our synthesis are cascade intermolecular and intramolecular Michael reactions, followed by epoxidation of the resultant hydroquinone with molecular oxygen.

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Detailed experimental procedures, characterization data, 1H and 13C NMR spectra, X-ray crystallographic data, and calculated and experimental CD spectra of (+)- and (−)-1. 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 15 publications.

  1. Glenn A. Pullella, Daniel Vuong, Ernest Lacey, Matthew J. Piggott. Total Synthesis of the Antitumor–Antitubercular 2,6′-Bijuglone Natural Product Diospyrin and Its 3,6′-Isomer. Journal of Natural Products 2020, 83 (12) , 3623-3634. https://doi.org/10.1021/acs.jnatprod.0c00800
  2. Saibal Sar, Jyoti Chauhan, Subhabrata Sen. Generation of Aryl Radicals from Aryl Hydrazines via Catalytic Iodine in Air: Arylation of Substituted 1,4-Naphthoquinones. ACS Omega 2020, 5 (8) , 4213-4222. https://doi.org/10.1021/acsomega.9b04014
  3. Kaixiu Luo, Yongqiang Zhao, Jiawei Zhang, Jia He, Rong Huang, Shengjiao Yan, Jun Lin, Yi Jin. Enantioselective Epoxypyrrolidines via a Tandem Cycloaddition/Autoxidation in Air and Mechanistic Studies. Organic Letters 2019, 21 (2) , 423-427. https://doi.org/10.1021/acs.orglett.8b03605
  4. Pravin Patil, Abhay Nimonkar, and Krishnacharya G. Akamanchi . Aryl-Free Radical-Mediated Oxidative Arylation of Naphthoquinones Using o-Iodoxybenzoic Acid and Phenylhydrazines and Its Application toward the Synthesis of Benzocarbazoledione. The Journal of Organic Chemistry 2014, 79 (5) , 2331-2336. https://doi.org/10.1021/jo500131h
  5. Mai Onuki, Motohiro Ota, Shoya Otokozawa, Shogo Kamo, Shusuke Tomoshige, Kazunori Tsubaki, Kouji Kuramochi. Dimerizations of 2-bromo-3-methyl-1,4-naphthoquinone and 2-methyl-1,4-naphthoquinone in tetra-n-butylammonium bromide. Tetrahedron 2020, 76 (6) , 130899. https://doi.org/10.1016/j.tet.2019.130899
  6. Chihiro Ito, Takuya Matsui, Makiko Takano, Tian-Shung Wu, Masataka Itoigawa. Anti-cell proliferation effect of naphthoquinone dimers isolated from Plumbago zeylanica. Natural Product Research 2018, 32 (18) , 2127-2132. https://doi.org/10.1080/14786419.2017.1366476
  7. Lauren A. M. Murray, Shaun M. K. McKinnie, Henry P. Pepper, Reto Erni, Zachary D. Miles, Michelle C. Cruickshank, Borja López-Pérez, Bradley S. Moore, Jonathan H. George. Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products. Angewandte Chemie 2018, 130 (34) , 11175-11180. https://doi.org/10.1002/ange.201804351
  8. Lauren A. M. Murray, Shaun M. K. McKinnie, Henry P. Pepper, Reto Erni, Zachary D. Miles, Michelle C. Cruickshank, Borja López-Pérez, Bradley S. Moore, Jonathan H. George. Total Synthesis Establishes the Biosynthetic Pathway to the Naphterpin and Marinone Natural Products. Angewandte Chemie International Edition 2018, 57 (34) , 11009-11014. https://doi.org/10.1002/anie.201804351
  9. Shogo Kamo, Kouji Kuramochi, Kazunori Tsubaki. Recent topics in total syntheses of natural dimeric naphthoquinone derivatives. Tetrahedron Letters 2018, 59 (3) , 224-230. https://doi.org/10.1016/j.tetlet.2017.12.040
  10. Juan Feng, Xiaoqiang Lei, Zhen Guo, Yefeng Tang. Total Synthesis of Homodimericin A. Angewandte Chemie 2017, 129 (27) , 8003-8007. https://doi.org/10.1002/ange.201702893
  11. Juan Feng, Xiaoqiang Lei, Zhen Guo, Yefeng Tang. Total Synthesis of Homodimericin A. Angewandte Chemie International Edition 2017, 56 (27) , 7895-7899. https://doi.org/10.1002/anie.201702893
  12. Shogo Kamo, Kai Yoshioka, Kouji Kuramochi, Kazunori Tsubaki. Total Syntheses of Juglorescein and Juglocombins A and B. Angewandte Chemie 2016, 128 (35) , 10473-10476. https://doi.org/10.1002/ange.201604765
  13. Shogo Kamo, Kai Yoshioka, Kouji Kuramochi, Kazunori Tsubaki. Total Syntheses of Juglorescein and Juglocombins A and B. Angewandte Chemie International Edition 2016, 55 (35) , 10317-10320. https://doi.org/10.1002/anie.201604765
  14. K. Thomas Finley. Quinones. 2016,,, 1-67. https://doi.org/10.1002/0471238961.1721091406091412.a02.pub3
  15. . Kirk-Othmer Encyclopedia of Chemical Technology. 2000,,https://doi.org/

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