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image of Strategy to Synthesize Kingianin: Biomimetic and Non-Biomimetic Approaches

Abstract

Kingianins are complex pentacyclic natural products isolated from the bark of . This article reviews synthetic routes for kingianins and their analogues. The reports of five research groups are grouped in biomimetic and non-biomimetic approaches, featuring the use of Diels-Alder and [2+2] ketene cycloaddition reactions. The most recent research by Six, Azmi reported the utilisation of [2+2]-ketene cycloaddition of key precursors for the synthesis of bicyclo[4.2.0]octanes as key precursors of kingianins. This research demonstrates the advantages of ketene chemistry by synthesising precursors. With this achievement, we look forward to extending this method to the synthesis of additional bicyclo[4.2.0]octane analogues to achieve the total synthesis of kingianins.

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2025-01-09
2025-04-25
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References

  1. Leverrier A. Dau M.E.T.H. Retailleau P. Awang K. Guéritte F. Litaudon M. Kingianin A: A new natural pentacyclic compound from Endiandra kingiana. Org. Lett. 2010 12 16 3638 3641 10.1021/ol101427m 20704409
    [Google Scholar]
  2. Leverrier A. Awang K. Guéritte F. Litaudon M. Pentacyclic polyketides from Endiandra kingiana as inhibitors of the Bcl-xL/Bak interaction. Phytochemistry 2011 72 11-12 1443 1452 10.1016/j.phytochem.2011.04.005 21550092
    [Google Scholar]
  3. Nicolaou K.C. Petasis N.A. Zipkin R.E. The endiandric acid cascade. Electrocyclizations in organic synthesis. 4. Biomimetic approach to endiandric acids A-G. Total synthesis and thermal studies. J. Am. Chem. Soc. 1982 104 20 5560 5562 10.1021/ja00384a080
    [Google Scholar]
  4. Sharma P. Ritson D.J. Burnley J. Moses J.E. A synthetic approach to kingianin A based on biosynthetic speculation. Chem. Commun. (Camb.) 2011 47 38 10605 10607 10.1039/c1cc13949e 21863194
    [Google Scholar]
  5. Ng S.M. Beaudry C.M. Trauner D. Intramolecular Diels-Alder reactions of 5-vinyl-1,3-cyclohexadienes. Org. Lett. 2003 5 10 1701 1704 10.1021/ol0343414 12735756
    [Google Scholar]
  6. Jacobsen M.F. Moses J.E. Adlington R.M. Baldwin J.E. The biomimetic synthesis of SNF4435C and SNF4435D, and the total synthesis of the polyene metabolites aureothin, N-acetyl-aureothamine and spectinabilin. Tetrahedron 2006 62 8 1675 1689 10.1016/j.tet.2005.11.058
    [Google Scholar]
  7. Eade S.J. Walter M.W. Byrne C. Odell B. Rodriguez R. Baldwin J.E. Adlington R.M. Moses J.E. Biomimetic synthesis of pyrone-derived natural products: exploring chemical pathways from a unique polyketide precursor. J. Org. Chem. 2008 73 13 4830 4839 10.1021/jo800220w 18517253
    [Google Scholar]
  8. Lim H.N. Parker K.A. Total synthesis of kingianin A. Org. Lett. 2013 15 2 398 401 10.1021/ol303388k 23273168
    [Google Scholar]
  9. Harirchian B. Bauld N.L. Cation radical Diels-Alder cycloadditions in organic synthesis. A formal total synthesis of (-)-.beta.-selinene. J. Am. Chem. Soc. 1989 111 5 1826 1828 10.1021/ja00187a041
    [Google Scholar]
  10. Lin S. Ischay M.A. Fry C.G. Yoon T.P. Radical cation Diels-Alder cycloadditions by visible light photocatalysis. J. Am. Chem. Soc. 2011 133 48 19350 19353 10.1021/ja2093579 22032252
    [Google Scholar]
  11. Ischay M.A. Yoon T.P. Accessing the synthetic chemistry of radical ions. Eur. J. Org. Chem. 2012 2012 18 3359 3372 10.1002/ejoc.201101071
    [Google Scholar]
  12. Gieseler A. Steckhan E. Wiest O. Knoch F. Photochemically induced radical-cation Diels-Alder reaction of indole and electron-rich dienes. J. Org. Chem. 1991 56 4 1405 1411 10.1021/jo00004a013
    [Google Scholar]
  13. Robles O. McDonald F.E. Convergent synthesis of fostriecin via selective alkene couplings and regioselective asymmetric dihydroxylation. Org. Lett. 2009 11 23 5498 5501 10.1021/ol902365n 19902969
    [Google Scholar]
  14. Drew S.L. Lawrence A.L. Sherburn M.S. Total Synthesis of Kingianins A, D, and F. Angew. Chem. Int. Ed. 2013 52 15 4221 4224 10.1002/anie.201210084 23468400
    [Google Scholar]
  15. Bellville D.J. Wirth D.W. Bauld N.L. Cation-radical catalyzed Diels-Alder reaction. J. Am. Chem. Soc. 1981 103 3 718 720 10.1021/ja00393a061
    [Google Scholar]
  16. Bandaranayake W.M. Banfield J.E. Black D.S.C. Postulated electrocyclic reactions leading to endiandric acid and related natural products. J. Chem. Soc. Chem. Commun. 1980 19 902 903 10.1039/c39800000902
    [Google Scholar]
  17. Beaudry C.M. Trauner D. Synthetic Studies toward SNF4435 C and SNF4435 D. Org. Lett. 2002 4 13 2221 2224 10.1021/ol026069o 12074672
    [Google Scholar]
  18. Moses J.E. Adlington R.M. Sir Jack Baldwin, FRS: biomimetic studies at Oxford. Chem. Commun. (Camb.) 2005 48 5945 5952 10.1039/b512961c 16333494
    [Google Scholar]
  19. Parker K.A. Lim Y.H. The total synthesis of (-)-SNF4435 C and (+)-SNF4435 D. J. Am. Chem. Soc. 2004 126 49 15968 15969 10.1021/ja044733l 15584723
    [Google Scholar]
  20. Nishihara Y. Ikegashira K. Hirabayashi K. Ando J. Mori A. Hiyama T. Coupling reactions of alkynylsilanes mediated by a Cu (I) salt: Novel syntheses of conjugate diynes and disubstituted ethynes. J. Org. Chem. 2000 65 6 1780 1787 10.1021/jo991686k 10814151
    [Google Scholar]
  21. Fiandanese V. Bottalico D. Marchese G. Punzi A. A straightforward synthesis of indole and benzofuran derivatives. Tetrahedron 2008 64 1 53 60 10.1016/j.tet.2007.10.100
    [Google Scholar]
  22. Lim H.N. Parker K.A. Intermolecular radical cation Diels-Alder (RCDA) reaction of bicyclooctadienes: Biomimetic formal total synthesis of kingianin A and total syntheses of kingianins D, F, H, and J. J. Org. Chem. 2014 79 3 919 926 10.1021/jo402082y 24372363
    [Google Scholar]
  23. Moore J.C. Davies E.S. Walsh D.A. Sharma P. Moses J.E. StephenáDavies Formal synthesis of kingianin A based upon a novel electrochemically-induced radical cation Diels–Alder reaction. Chem. Commun. (Camb.) 2014 50 83 12523 12525 10.1039/C4CC05906A 25196219
    [Google Scholar]
  24. Nigenda S.E. Schleich D.M. Narang S.C. Keumi T. Electrochemical oxidation of 1,3‐Cyclohexadiene. J. Electrochem. Soc. 1987 134 10 2465 2470 10.1149/1.2100222
    [Google Scholar]
  25. Zhao J. Chen Q. Lu P. Zhang J. Yan P. Wang Z. Total synthesis of (+)-Kingianin A by Enantioselective Cycloaddition of strained Cyclobutenone. Synthesis 2022 54 8 1977 1982 10.1055/s‑0041‑1737339
    [Google Scholar]
  26. Yan P. Zhong C. Zhang J. Liu Y. Fang H. Lu P. 3‐(Methoxycarbonyl)Cyclobutenone as a reactive Dienophile in Enantioselective Diels–Alder reactions catalyzed by Chiral Oxazaborolidinium Ions. Angew. Chem. Int. Ed. 2021 60 9 4609 4613 10.1002/anie.202014308 33201584
    [Google Scholar]
  27. Mohamad Taib M.N.A. Litaudon M. Awang K. Six Y. Synthesis of bicyclo[4.2.0]octane ring of kingianin via [2+2] ketene cycloaddition. Organic Commun 2024 17 1 56 62 10.25135/acg.oc.164.2402.3124
    [Google Scholar]
  28. Staudinger H. Ketenes, a new body class. EurJIC. 1905 38 2 1735 1739 10.1002/cber.19050380283
    [Google Scholar]
  29. Tidwell T.T. The first century of ketenes (1905-2005): The birth of a versatile family of reactive intermediates. Angew. Chem. Int. Ed. 2005 44 36 5778 5785 10.1002/anie.200500098 16149113
    [Google Scholar]
  30. Tidwell T.T. Ketene chemistry after 100 years: Ready for a new century. Eur. J. Org. Chem. 2006 2006 3 563 576 10.1002/ejoc.200500452
    [Google Scholar]
  31. Wu H.Y. Walker K.A.M. Nelson J.T. Stereochemical consequences of 6-and 8-substitution in reactions of bicyclo [4.2. 0] octan-7-ones. J. Org. Chem. 1994 59 6 1389 1395 10.1021/jo00085a031
    [Google Scholar]
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