A much improved synthesis of the siderophore enterobactin

Enterobactin, the cyclic trimer of N-(2,3-dihydroxybenzoyl)-L-serine has been efficiently prepared. A simple and high yield procedure has been developed for construction of N-protected serine trilactone as the key intermediate: methyl N-trityl-L-serinate and 2,2-dibutyl-1,3,2-dioxastannolane were re...

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Bibliographic Details
Published in:Tetrahedron letters 1997-02, Vol.38 (5), p.749-752
Main Authors: Ramirez, Robert J.A., Karamanukyan, Levon, Ortiz, Steven, Gutierrez, Carlos G.
Format: Article
Language:English
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Summary:Enterobactin, the cyclic trimer of N-(2,3-dihydroxybenzoyl)-L-serine has been efficiently prepared. A simple and high yield procedure has been developed for construction of N-protected serine trilactone as the key intermediate: methyl N-trityl-L-serinate and 2,2-dibutyl-1,3,2-dioxastannolane were refluxed in xylene to produce the triolide as the only lactone product in 85% yield. Cyclooligomerization of methyl N-trityl-L-serinate efficiently produced triolide 3 (85%), which was then converted into enterobactin.
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(96)02452-5