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Title

An improved synthesis of the antibiotic dehydrophos

AuthorsJiménez-Andreu, M. Mercedes; Sayago, Francisco J. CSIC ORCID; Cativiela, Carlos CSIC ORCID
Issue Date2018
PublisherWiley-VCH
CitationEuropean Journal of Organic Chemistry (29): 3965–3973 (2018)
AbstractWithin this work an efficient procedure for the synthesis of the vinyl phosphonate tripeptide dehydrophos is described. This procedure constitutes a significant improvement over previously described strategies, since critical transformations in the synthesis of dehydrophos were carried out in only two synthetic steps, with higher yields and under smooth conditions. Thus, the dehydrophosphoalanine residue was generated by means of the Horner–Wadsworth–Emmons reaction of formaldehyde with a peptide bearing an aminomethylbis(phosphonate) moiety, whereas deprotection of the N‐terminal position of the thus‐obtained dehydrophosphonopeptide and partial hydrolysis of the dimethyl phosphonate residue took place simultaneously. In addition, we confirmed that the chiral integrity of the leucine residue was preserved throughout these transformations.
Publisher version (URL)https://doi.org/10.1002/ejoc.201800689
URIhttp://hdl.handle.net/10261/185127
DOI10.1002/ejoc.201800689
ISSN1434-193X
E-ISSN1099-0690
Appears in Collections:(ISQCH) Artículos

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