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Azido and desamino analogs of the marine natural product oroidin

  • Lisa Anders and Thomas Lindel
Published/Copyright: March 8, 2023
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Zeitschrift für Naturforschung B
From the journal Zeitschrift für Naturforschung B Volume 78 Issue 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.

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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

Articles in the same Issue

  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
Keywords for this article
azido compounds; click chemistry; heterocycles; marine natural products; pyrrole–imidazole alkaloids

Articles in the same Issue

  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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