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Cover Feature: Short‐Cut Bio‐Inspired Synthesis of Tricyclic Guanidinic Motifs of Crambescidins and Batzelladines Marine Alkaloids (Eur. J. Org. Chem. 35/2020)
Author(s) -
ElDemerdash Amr,
Ermolenko Ludmila,
Gros Emmanuelle,
Retailleau Pascal,
Thanh Binh Nguyen,
GauvinBialecki Anne,
AlMourabit Ali
Publication year - 2020
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.202001187
Subject(s) - sponge , chemistry , diastereomer , tricyclic , biomimetic synthesis , stereochemistry , guanidine , cover (algebra) , alkaloid , combinatorial chemistry , organic chemistry , botany , biology , mechanical engineering , engineering
The Cover Feature shows a 4 steps short‐cut bio‐inspired synthetic tactic for the synthesis of the fused tricyclic guanidinic core of complex polycyclic crambescidine and batzelladine metabolites isolated from marine sponges of the orders Poecilosclerida and Axinellida. The synthetic strategy mirrors Robinson–Schöepf tropinone biomimetic synthesis together with the biomechanistic analysis of the isolated marine metabolites. The application of this strategy led to two unnatural diastereoisomers of merobatzelladine B, an anti‐infective tricyclic guanidine alkaloid, isolated from the marine sponge Monanchora sp. More information can be found in the Full Paper by A. Al‐Mourabit et al.