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Article Dans Une Revue Tetrahedron Letters Année : 2010

Synthesis of the trans-fusarinine scaffold

Résumé

The trans-fusarinine backbone is a common feature encountered in many fungal siderophores. This monomer is notably the structural base of Nα-methyl coprogen B and dimerumic acid. Both siderophores are known to be secreted by Scedosporium apiospermum, an emerging pathogenic fungus studied for its high involvement in invasive infections of immunocompromised patients. The strategy developed here for the synthesis of the trans-fusarinine scaffold relies on the preparation of both N-hydroxyornithine and 3-anhydroxymevalonic acid subunits starting from l-ornithine and 3-butyn-1-ol, respectively. The coupling of these two building blocks led to the expected protected backbone.

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Dates et versions

hal-03247640 , version 1 (03-06-2021)

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Samuel Bertrand, Olivier Duval, Jean-Jacques Helesbeux, Gérald Larcher, Pascal Richomme. Synthesis of the trans-fusarinine scaffold. Tetrahedron Letters, 2010, 51 (16), pp.2119 - 2122. ⟨10.1016/j.tetlet.2010.02.058⟩. ⟨hal-03247640⟩

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