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Natural Product Biosynthesis Via the Diels-Alder Reaction

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Secondary-Metabolite Biosynthesis and Metabolism

Part of the book series: Environmental Science Research ((ESRH,volume 44))

Abstract

The Diels-Alder reaction is named after the German chemists Otto Diels and Kurt Alder of the University of Kiel. The awarding of the 1950 Nobel Prize in chemistry to these scientists attests to the importance and broad application of this reaction. Fringuelli and Taticchi have recently reviewed the reaction1.

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Literature

  1. F. Fringuelli and A. Taticchi, “Dienes in the Diels-Alder Reaction,” Wiley Interscience, N. Y. (1990).

    Google Scholar 

  2. J. P. Kutney, T. Inaba and D. L. Dreyer, The structure of thamnosin. A novel dimeric coumarin system, J. Amer. Chem. Soc. 90:813 (1968).

    Article  CAS  Google Scholar 

  3. G. C. Brophy, J. Mohandas, M. Slaytor, S. Sternhell, T. R. Watson and L. A. Wilson, Novel lignans from a Cinnamomum sp. from Bougainville. Tetrahed. Lett. 5159 (1969).

    Google Scholar 

  4. I. Mori and Y. Nakachi, Isolation and structure of alflabene from Alpinia flabellata Ridl., Tetrahed. Lett. 2297 (1978).

    Google Scholar 

  5. 5 L. Jurd and R. Y. Wong, New Quinoline alkaloids from the heartwood of Euxylophora paraensis. Aust. J. Chem. 34:1625 (1981).

    Article  CAS  Google Scholar 

  6. L. Jurd, R. Y. Wong and M. Benson, The structure of paraensidimerin A and C, two bisquinolinone alkaloids from Euxylophora paraensis. Aust. J. Chem. 35:2505 (1982).

    Article  CAS  Google Scholar 

  7. W. Oppolzer, Intramolecular [4 + 2] and [3 + 2] cyclo additions in organic synthesis, Angew. Chem. Int. Ed. Engl. 16:10 (1977).

    Article  Google Scholar 

  8. R. D. Stipanovic, A. A. Bell, D. H. O’Brien and M. J. Lukefahr, Heliocide H2:an insecticidal sesterterpenoid from cotton (Gossypium). Tetrahed. Lett. 567 (1977).

    Google Scholar 

  9. R. D. Stipanovic, A. A. Bell, D. H. O’Brien and M. J. Lukefahr, Heliocide H1:A new insecticidal C25 terpenoid from cotton (Gossypium hirsutum). J. Agri. Food Chem. 26:115 (1978).

    Article  CAS  Google Scholar 

  10. R. D. Stipanovic, A. A. Bell, D. H. O’Brien and M. J. Lukefahr, Heliocide H3: an insecticidal terpenoid from Gossypium hirsutum. Phytochemistry 17:151 (1978).

    Article  CAS  Google Scholar 

  11. H. J. Williams, R. D. Stipanovic, L. A. Smith, S. B. Vinson, P. O. Darnell, R. Montandon, D. L. Begin, G. W. Elzen, H. Gunasena and A. A. Bell, Effects of gossypol and other terpenoids on Heliothis virescens development, Rev. Latinoamer. Quim. 18:119 (1987).

    CAS  Google Scholar 

  12. A. A. Bell, R. D. Stipanovic, D. H. O’Brien and P. A. Fryxell, Sesquiterpenoid aldehyde quinones and derivatives in pigment glands of Gossypium. Phytochemistry 17:1297 (1978).

    Article  CAS  Google Scholar 

  13. J. R. Gray, T. J. Mabry, A. A. Bell, R. D. Stipanovic and M. J. Lukefahr,para-Hemigossypolone: a sesquiterpenoid aldehyde quinone from Gossypium hirsutum. J. Chem. Soc., Chem. Comm. 109 (1976).

    Google Scholar 

  14. G. W. Elzen, H. J. Williams, A. A. Bell, R. D. Stipanovic and S. B. Vinson,Quantification of volatile terpenes of glanded and glandless Gossypium hirsutum L. cultivars and lines by gas chromatography, J. Agri. Food Chem. 33:1079 (1985).

    Article  CAS  Google Scholar 

  15. A. A. Bell, R. D. Stipanovic, G. W. Elzen and H. J. Williams, Structural and genetic variation of natural pesticides in pigment glands of cotton (Gossypium). in: “ Allelochemicals: Role in Agriculture and Forestry.” G. R. Waller, ed., ACS Symposium Series 330, Amer. Chem. Soc., Washington, DC, (1987).

    Google Scholar 

  16. A. A. Bell and R. D. Stipanovic, The chemical composition, biological activity, and genetics of pigment glands in cotton, in: “Beltwide Cotton Prod. Res. Conf.” J.M. Brown, ed., National Cotton Council of America, Memphis (1977).

    Google Scholar 

  17. D.W. Altman, R.D. Stipanovic and A.A. Bell, Terpenoids in foliar pigment glands of A, D, and AD genome cottons: introgression potential for pest resistance, J. Heredity 81:447 (1990).

    CAS  Google Scholar 

  18. R. D. Stipanovic, D. W. Altman, D. W. Begin, G. A. Greenblatt and J. H.Benedict, Terpenoid aldehydes in Upland cotton: analysis by aniline and HPLC methods, J. Agri. Food Chem. 36:509 (1988).

    Article  CAS  Google Scholar 

  19. P. V. Alston and R. M. Ottenbrite, Secondary orbital interactions determining regioselectivity in the Lewis acid catalyzed Diels-Alder reaction. II, J. Org. Chem, 40:1111 (1975).

    Article  CAS  Google Scholar 

  20. A. Hosomi, H. Iguchi, J. Sasaki and H. Sakurai, Highly regioselective Diels-Alder reactions of 2-trimethylsilylmethyl-1,3-butadiene catalyzed by a Lewis acid and application to syntheses of terpenes, Tetrahed. Lett. 23:551 (1982).

    Article  CAS  Google Scholar 

  21. F. Fringuelli, F. Pizzo, A. Taticchi, T. D. J. Halls and E. Wenkert, Diels-Alder reactions of cycloalkenones. 1. Preparation and structure of the adducts, J. Org. Chem. 47:5056 (1982).

    Article  CAS  Google Scholar 

  22. T. Nomura, Phenolic compounds of the mulberry tree and related plants. in: “Progress in the Chemistry of Organic Natural Products,” W. Herz, H. Grisebach, G. W. Kirby and Ch. Tamm, eds., Springer-Verlag, N. Y. (1988).

    Google Scholar 

  23. T. Nomura, T. Fukai, T. Narita, S. Terada, J. Uzawa, Y. Iitaka, M. Takasugi, S. Ishikawa, S. Nagao and T. Masamune, Confirmation of the structures of kuwanones G and H (albanins F and G) by partial synthesis, Tetrahed. Lett. 22:2195 (1981).

    Article  CAS  Google Scholar 

  24. J. Sauer and R. Sustmann, Mechanistic aspects of Diels-Alder reactions: a critical survey, Angew. Chem. Int. Ed. Engl. 19:779 (1980).

    Article  Google Scholar 

  25. I. Fleming, “Frontier Orbitals and Organics Chemical Reactions,” Wiley, N. Y.(1976).

    Google Scholar 

  26. A. Wassermann, The mechanism of additions to double bonds. Part II. The steric course of two diene syntheses, J. Chem. Soc. 825:1511 (1935).

    Article  Google Scholar 

  27. R. B. Woodward and H. Baer, Studies on diene-addition reactions. II. The reaction of 6,6-pentamethylenefulvene with maleic anahydride, J. Amer. Chem. Soc. 66:645 (1944).

    Article  CAS  Google Scholar 

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© 1992 Springer Science+Business Media New York

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Stipanovic, R.D. (1992). Natural Product Biosynthesis Via the Diels-Alder Reaction. In: Petroski, R.J., McCormick, S.P. (eds) Secondary-Metabolite Biosynthesis and Metabolism. Environmental Science Research, vol 44. Springer, Boston, MA. https://doi.org/10.1007/978-1-4615-3012-1_22

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  • DOI: https://doi.org/10.1007/978-1-4615-3012-1_22

  • Publisher Name: Springer, Boston, MA

  • Print ISBN: 978-1-4613-6312-5

  • Online ISBN: 978-1-4615-3012-1

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