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Azido and desamino analogs of the marine natural product oroidin

  • Lisa Anders und Thomas Lindel
Veröffentlicht/Copyright: 8. März 2023
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Zeitschrift für Naturforschung B
Aus der Zeitschrift Zeitschrift für Naturforschung B Band 78 Heft 3-4

Abstract

As part of our program on the synthesis and reactivity of the pyrrole-imidazole alkaloids from marine sponges, the synthesis of the 2-azido analog of the key marine natural product oroidin is reported. In addition, desaminooroidin and its alkyne analog were synthesized. Red-Al reduction of a 4-alkynylimidazole intermediate afforded the (E)-alkene, without having to pass via the (Z)-alkene. Coupling of 4,5-dibromopyrrole-2-carboxylic acid with 2-azidoimidazolylprop-2-en-1-amine was best achieved by EDCI-mediated coupling, which was superior to using the corresponding trichloromethylketone. Use of t-BuOK in acetonitrile can be recommended for the coupling of non-azidated alkenyl and alkynylimidazoles. The azido analog of oroidin underwent click cycloadditions to imidazolyltriazoles.

Keywords: azido compounds; click chemistry; heterocycles; marine natural products; pyrrole–imidazole alkaloids

Dedicated to Professor Gerhard Müller on the occasion of his 70th birthday.

Corresponding author: Thomas Lindel, TU Braunschweig, Institute of Organic Chemistry, Hagenring 30, 38106 Braunschweig, Germany, E-mail:

Acknowledgement

TU Braunschweig is thanked for financial support. Vincent Malecha and Johanna Rödiger are thanked for laboratory assistance.

  1. Author contributions: All the authors have accepted responsibility for the entire content of this submitted manuscript and approved submission.

  2. Research funding: None declared.

  3. Conflict of interest statement: The authors declare no conflicts of interest regarding this article.

References

1(a). Forenza, S., Minale, L., Riccio, R., Fattorusso, E. J. Chem. Soc., Chem. Commun. 1971, 1129–1130.10.1039/c29710001129Suche in Google Scholar

(b) Garcia, E. E., Benjamin, L. E., Frye, R. I. J. Chem. Soc., Chem. Commun. 1973, 78–79.10.1039/c39730000078Suche in Google Scholar

2. Lindel, T. Alkaloids Chem. Biol. 2017, 77, 117–219; https://doi.org/10.1016/bs.alkal.2016.12.001.Suche in Google Scholar PubMed

3. Al-Mourabit, A., Zancanella, M. A., Tilvi, S., Romo, D. Nat. Prod. Rep. 2011, 28, 1229–1260; https://doi.org/10.1039/c0np00013b.Suche in Google Scholar PubMed PubMed Central

4. Pöverlein, C., Breckle, G., Lindel, T. Org. Lett. 2006, 8, 819–821; https://doi.org/10.1021/ol0526219.Suche in Google Scholar PubMed

5. Lejeune, C., Tian, H., Appenzeller, J., Ermolenko, L., Martin, M.-T., Al-Mourabit, A. J. Nat. Prod. 2013, 76, 903–908; https://doi.org/10.1021/np400048r.Suche in Google Scholar PubMed

6. Lindel, T., Breckle, G., Hochgürtel, M., Volk, C., Grube, A., Köck, M. Tetrahedron Lett. 2004, 45, 8149–8152; https://doi.org/10.1016/j.tetlet.2004.09.048.Suche in Google Scholar

7. Barrios Sosa, A. C., Yakushijin, K., Horne, D. A. Org. Lett. 2000, 2, 3443–3444; https://doi.org/10.1021/ol000233v.Suche in Google Scholar PubMed

8. Stout, P. E., Morinaka, B. I., Wang, Y.-G., Romo, D., Molinski, T. F. J. Nat. Prod. 2012, 75, 527–530; https://doi.org/10.1021/np300051k.Suche in Google Scholar PubMed PubMed Central

9. Stout, P. E., Wang, Y.-G., Romo, D., Molinski, T. F. Angew. Chem. Int. Ed. 2012, 51, 4877–4881; https://doi.org/10.1002/anie.201108119.Suche in Google Scholar PubMed PubMed Central

10. Gadosy, T. A., McClelland, R. A. J. Am. Chem. Soc. 1999, 121, 1459–1465; https://doi.org/10.1021/ja9827090.Suche in Google Scholar

11. Polshakov, D., Rai, S., Wilson, R. M., Mack, E. T., Vogel, M., Krause, J. A., Burdzinski, G., Platz, M. S. Biochemistry 2005, 44, 11241–11253; https://doi.org/10.1021/bi050859z.Suche in Google Scholar PubMed

12. Nilov, D. I., Komarov, D. Y., Panov, M. S., Karabaeva, K. E., Mereshchenko, A. S., Tarnovsky, A. N., Wilson, R. M. J. Am. Chem. Soc. 2013, 135, 3423–3438; https://doi.org/10.1021/ja3068148.Suche in Google Scholar PubMed

13. Sudakow, A., Jones, P. G., Lindel, T. Eur. J. Org. Chem. 2012, 681–684.10.1002/ejoc.201101711Suche in Google Scholar

14. Sudakow, A., Papke, U., Lindel, T. Chem. Eur. J. 2014, 20, 10223–10226; https://doi.org/10.1002/chem.201402959.Suche in Google Scholar PubMed

15. Kanitz, N. E., Lindel, T. Z. Naturforsch. 2016, 71b, 1287–1300.10.1515/znb-2016-0195Suche in Google Scholar

16. Kanitz, N. E., Fresia, M., Jones, P. G., Lindel, T. Eur. J. Org. Chem. 2021, 3573–3578.10.1002/ejoc.202100603Suche in Google Scholar

17. Breckle, G., Polborn, K., Lindel, T. Z. Naturforsch. 2003, 58b, 451–456.10.1515/znb-2003-0516Suche in Google Scholar

18. Wang, Y.-G., Morinaka, B. I., Reyns, J. C. P., Wolff, J. J., Romo, D., Molinski, T. F. J. Nat. Prod. 2010, 73, 428–434; https://doi.org/10.1021/np900638e.Suche in Google Scholar PubMed PubMed Central

19. Berrée, F., Bleis, P. G.-L., Carboni, B. Tetrahedron Lett. 2002, 43, 4935–4938; https://doi.org/10.1016/s0040-4039(02)00947-4.Suche in Google Scholar

20. Kirk, K. L. J. Heterocycl. Chem. 1985, 22, 57–59.10.1002/jhet.5570220115Suche in Google Scholar

21. Hochgürtel, M., Lindel, T. J. Org. Chem. 2000, 65, 2806–2809; https://doi.org/10.1021/jo991395b.Suche in Google Scholar PubMed

22. Ollivier, N., Dheur, J., Mhidia, R., Blanpain, A., Melnyk, O. Org. Lett. 2010, 12, 5238–5241; https://doi.org/10.1021/ol102273u.Suche in Google Scholar PubMed

23. Alkorta, I., Blanco, F., Elguero, J. Tetrahedron 2010, 66, 5071–5081; https://doi.org/10.1016/j.tet.2010.04.119.Suche in Google Scholar

24. Zidar, N., Žula, A., Tomašič, T., Rogers, M., Kirby, R. W., Tytgat, J., Peigneur, S., Kikelj, D., Ilaš, J., Mašič, L. P. Eur. J. Med. Chem. 2017, 139, 232–241; https://doi.org/10.1016/j.ejmech.2017.08.015.Suche in Google Scholar PubMed

Supplementary Material

This article contains supplementary material (https://doi.org/10.1515/znb-2023-0305).

Received: 2023-02-03
Accepted: 2023-02-07
Published Online: 2023-03-08
Published in Print: 2023-03-28

© 2023 Walter de Gruyter GmbH, Berlin/Boston

Artikel in diesem Heft

  1. Frontmatter
  2. In this issue
  3. Preface
  4. Professor Dr. Gerhard Müller. Editor-in-Chief der Zeitschrift für Naturforschung B – Chemical Sciences. zum 70. Geburtstag
  5. Research Articles
  6. Ferrocenylmethylation of theophylline
  7. Electron density of a cyclic tetrasaccharide composed of benzoylated galactose units
  8. Orthoamide und Iminiumsalze, CIX. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Diolen, Ethandithiol und CH-aciden Nitroverbindungen
  9. 1,4-Divinylphenylene-bridged diruthenium complexes with 2-hydroxypyridine- and 2- or 8-hydroxyquinoline-olate ligands
  10. The calcium oxidotellurates Ca2(TeIVTeVIO7), Ca2(TeIVO3)Cl2 and Ca5(TeIVO3)4Cl2 obtained from salt melts
  11. N-heterocyclic carbene-mediated oxidation of copper(I) in an imidazolium ionic liquid
  12. Synthesis, crystal structure, thermal and spectroscopic properties of ZnX2-2-methylpyrazine (X = Cl, Br, I) coordination compounds
  13. Solid-state molecular structures of Se(IV) and Te(IV) dihalides X2Se(CH3)(C6F5) and the gas-phase structure of Se(CH3)(C6F5)
  14. Ein neuartiger T-förmiger 14-Elektronen-Iridium(I)-Komplex stabilisiert durch eine agostische Ir–H-Wechselwirkung
  15. Exploring dicyanamides with two different alkali-metal cations: phase separations, solid solutions and the new compound Rb1.667Cs0.333[N(CN)2]2
  16. Eu4Al13Pt9 – a coloring variant of the Ho4Ir13Ge9 type structure
  17. Decoration of the [Nb6O19]8– cluster shell with six Cu2+-centred complexes generates the [(Cu(cyclen))6Nb6O19]4+ moiety: room temperature synthesis, crystal structure and selected properties
  18. Structure and spectroscopic properties of etherates of the beryllium halides
  19. The palladium-rich silicides RE3Pd20Si6 (RE = Sc, Y and Lu)
  20. Azido and desamino analogs of the marine natural product oroidin
  21. High-pressure high-temperature preparation of CeGe3
  22. On the synthesis and crystal structure of praseodymium(III) metaborate molybdate(VI) – PrBO2MoO4
  23. A third polymorph of the zwitterionic complex trichlorido-((dimethylphosphoryl)methanaminium-κO)zinc(II)
  24. Mechanochemical synthesis and structural evaluation of a metastable polymorph of Ti3Sn
  25. Synthesis and application of calcium silicate hydrate (C-S-H) nanoparticles for early strength enhancement by eco-friendly low carbon binders
  26. Sterically crowded di-indazolyl-pyridines: Iron(II) complexation studies
https://doi.org/10.1515/znb-2023-0305
Schlagwörter für diesen Artikel
azido compounds; click chemistry; heterocycles; marine natural products; pyrrole–imidazole alkaloids

Artikel in diesem Heft

  1. Frontmatter
  2. In this issue
  3. Preface
  4. Professor Dr. Gerhard Müller. Editor-in-Chief der Zeitschrift für Naturforschung B – Chemical Sciences. zum 70. Geburtstag
  5. Research Articles
  6. Ferrocenylmethylation of theophylline
  7. Electron density of a cyclic tetrasaccharide composed of benzoylated galactose units
  8. Orthoamide und Iminiumsalze, CIX. Umsetzungen von Orthoamiden der Alkincarbonsäuren mit Diolen, Ethandithiol und CH-aciden Nitroverbindungen
  9. 1,4-Divinylphenylene-bridged diruthenium complexes with 2-hydroxypyridine- and 2- or 8-hydroxyquinoline-olate ligands
  10. The calcium oxidotellurates Ca2(TeIVTeVIO7), Ca2(TeIVO3)Cl2 and Ca5(TeIVO3)4Cl2 obtained from salt melts
  11. N-heterocyclic carbene-mediated oxidation of copper(I) in an imidazolium ionic liquid
  12. Synthesis, crystal structure, thermal and spectroscopic properties of ZnX2-2-methylpyrazine (X = Cl, Br, I) coordination compounds
  13. Solid-state molecular structures of Se(IV) and Te(IV) dihalides X2Se(CH3)(C6F5) and the gas-phase structure of Se(CH3)(C6F5)
  14. Ein neuartiger T-förmiger 14-Elektronen-Iridium(I)-Komplex stabilisiert durch eine agostische Ir–H-Wechselwirkung
  15. Exploring dicyanamides with two different alkali-metal cations: phase separations, solid solutions and the new compound Rb1.667Cs0.333[N(CN)2]2
  16. Eu4Al13Pt9 – a coloring variant of the Ho4Ir13Ge9 type structure
  17. Decoration of the [Nb6O19]8– cluster shell with six Cu2+-centred complexes generates the [(Cu(cyclen))6Nb6O19]4+ moiety: room temperature synthesis, crystal structure and selected properties
  18. Structure and spectroscopic properties of etherates of the beryllium halides
  19. The palladium-rich silicides RE3Pd20Si6 (RE = Sc, Y and Lu)
  20. Azido and desamino analogs of the marine natural product oroidin
  21. High-pressure high-temperature preparation of CeGe3
  22. On the synthesis and crystal structure of praseodymium(III) metaborate molybdate(VI) – PrBO2MoO4
  23. A third polymorph of the zwitterionic complex trichlorido-((dimethylphosphoryl)methanaminium-κO)zinc(II)
  24. Mechanochemical synthesis and structural evaluation of a metastable polymorph of Ti3Sn
  25. Synthesis and application of calcium silicate hydrate (C-S-H) nanoparticles for early strength enhancement by eco-friendly low carbon binders
  26. Sterically crowded di-indazolyl-pyridines: Iron(II) complexation studies
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