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Intramolecular Diels−Alder and Cope Reactions of o-Quinonoid Monoketals and Their Adducts:  Efficient Syntheses of (±)-Xestoquinone and Heterocycles Related to Viridin

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Guelph-Waterloo Center for Graduate Work in Chemistry, University of Waterloo, Waterloo, Ontario N2L 3G1, Canada
Department of Chemistry, Wilfrid Laurier University, Waterloo, Ontario N2L 3C5, Canada
Cite this: J. Org. Chem. 1997, 62, 8, 2330–2331
Publication Date (Web):April 18, 1997
https://doi.org/10.1021/jo970394l
Copyright © 1997 American Chemical Society
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General experimental procedures are described for the intramolecular Diels−Alder (IMDA) reaction forming adducts 6a−c, 7a−c, 10a−c, 13a,b, 14, and 16 and for the Cope rearrangement of 6a to 7a. Copies of 1H NMR spectra are provided for compounds 6a−c, 7a−c, 10a−c (endo and exo), 13a (endo and exo), 13b, 14, 16 (endo and exo), and 17 (20 pages).

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This article is cited by 46 publications.

  1. Yingbo Shi, Yang Ji, Kunyun Xin, and Shuanhu Gao . Total Synthesis of (−)-Xestosaprol N and O. Organic Letters 2018, 20 (3) , 732-735. https://doi.org/10.1021/acs.orglett.7b03865
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  4. Jihong Gao, Josephine Orso Simon, Russell Rodrigo, and Abdeljalil Assoud . From Chiral ortho-Benzoquinone Monoketals to Nonracemic Indolinocodeines through Diels–Alder and Cope Reactions. The Journal of Organic Chemistry 2013, 78 (1) , 48-58. https://doi.org/10.1021/jo3014098
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  12. Chien-Hsing Chen,, Polisetti Dharma Rao, and, Chun-Chen Liao. Furans Act as Dienophiles in Facile Diels−Alder Reactions with Masked o-Benzoquinones. Journal of the American Chemical Society 1998, 120 (50) , 13254-13255. https://doi.org/10.1021/ja982974l
  13. Xiao-Long Lu, Yuanyou Qiu, Baochao Yang, Haibing He, Shuanhu Gao. Asymmetric total synthesis of (+)-xestoquinone and (+)-adociaquinones A and B. Chemical Science 2021, 12 (13) , 4747-4752. https://doi.org/10.1039/D0SC07089K
  14. Bidyut Kumar Senapati. Recent progress in the synthesis of the furanosteroid family of natural products. Organic Chemistry Frontiers 2021, 26 https://doi.org/10.1039/D0QO01454K
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  16. Gregg M. Schwarzwalder, Christopher D. Vanderwal. Strategies for the Synthesis of the Halenaquinol and Xestoquinol Families of Natural Products. European Journal of Organic Chemistry 2017, 2017 (12) , 1567-1577. https://doi.org/10.1002/ejoc.201601418
  17. Yan-Bin Lu, Day-Shin Hsu, Chun-Chen Liao. Rapid construction of polycyclic ring systems from aromatics: stereoselective synthesis of the carbon framework of vinigrol. Tetrahedron Letters 2014, 55 (38) , 5315-5318. https://doi.org/10.1016/j.tetlet.2014.07.064
  18. Vimal Varghese, Tomas Hudlicky. Short Chemoenzymatic Total Synthesis of ent -Hydromorphone: An Oxidative Dearomatization/Intramolecular [4+2] Cycloaddition/Amination Sequence. Angewandte Chemie 2014, 126 (17) , 4444-4447. https://doi.org/10.1002/ange.201400286
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  45. R. CARLINI, K. HIGGS, C. OLDER, S. RANDHAWA, R. RODRIGO. ChemInform Abstract: Intramolecular Diels-Alder and Cope Reactions of o-Quinonoid Monoketals and Their Adducts: Efficient Syntheses of (.+-.)- Xestoquinone and Heterocycles Related to Viridin.. ChemInform 1997, 28 (36) , no-no. https://doi.org/10.1002/chin.199736051
  46. Nurullah Saracoglu. Functionalization of Indole and Pyrrole Cores via Michael-Type Additions. ,,, 1-61. https://doi.org/10.1007/7081_2007_073

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