Short-cut bio-inspired synthesis of tricyclic guanidinic motifs of crambescidins and batzelladines marine alkaloids

El-Demerdash, Amr ORCID: https://orcid.org/0000-0001-6459-2955, Ermolenko, Ludmila, Gros, Emmanuelle, Retailleau, Pascal, Thanh, Binh Nguyen, Gauvin-Bialecki, Anne and Al-Mourabit, Ali (2020) Short-cut bio-inspired synthesis of tricyclic guanidinic motifs of crambescidins and batzelladines marine alkaloids. European Journal of Organic Chemistry, 2020 (35). pp. 5677-5684. ISSN 1434-193X

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Abstract

We report a convenient short synthesis of tricyclic guanidine-containing natural products model featuring four-component reaction between 2,5-dimethoxytetrahydrofuran, 2-aminopyrimidine and two acylacetic or benzoylacetic acids. A synthetic route combining the Robinson–Schöepf bioinspired strategy and biomechanistic analysis of the crambescidin and batzelladine alkaloids family. An application of this strategy to the synthesis of two unnatural stereoisomers of merobatzelladine B is described from the protected guanidine in the form of aminopyrimidine.

Item Type:	Article
Additional Information:	Funding Information: Financial support from CNRS is gratefully acknowledged. The authors thank the ANR (POMARE project, 2011‐EBIM‐006‐01). A. El‐Demerdash's PhD was granted and financed by the Egyptian Government (Ministry of Higher Education), they are gratefully acknowledged. Special thanks for J‐F. Gallard for technical assistance and NMR measurements. Remerciement Robert Dodd Funding Information: Financial support from CNRS is gratefully acknowledged. The authors thank the ANR (POMARE project, 2011-EBIM-006-01). A. El-Demerdash's PhD was granted and financed by the Egyptian Government (Ministry of Higher Education), they are gratefully acknowledged. Special thanks for J-F. Gallard for technical assistance and NMR measurements. Remerciement Robert Dodd Publisher Copyright: © 2020 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Uncontrolled Keywords:	batzelladines,bioactivity,crambescidins,guanidine alkaloids,multicomponent reactions,physical and theoretical chemistry,organic chemistry,sdg 14 - life below water ,/dk/atira/pure/subjectarea/asjc/1600/1606
Faculty \ School:	Faculty of Science > School of Pharmacy (former - to 2024)
Related URLs:	http://www.scopus.com/inward/record.url?...
Depositing User:	LivePure Connector
Date Deposited:	05 Aug 2024 11:32
Last Modified:	25 Sep 2024 17:59
URI:	https://ueaeprints.uea.ac.uk/id/eprint/96132
DOI:	10.1002/ejoc.202000744

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