Syntheses of brostallicin starting from distamycin A

Two syntheses of brostallicin, a DNA minor groove binder now undergoing phase II studies, starting from distamycin A are described. One approach is based upon the selective hydrolysis via imide activation of the C-terminus amide. Besides employing traditional solution-phase synthesis, the convenient...

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Bibliographic Details
Published in:Tetrahedron letters 2002-10, Vol.43 (41), p.7323-7327
Main Authors: Beria, Italo, Nesi, Marcella
Format: Article
Language:English
Subjects:
brostallicin
Curtius rearrangement
diphenyl phosphorazidate
distamycin A
minor groove binders
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Summary:Two syntheses of brostallicin, a DNA minor groove binder now undergoing phase II studies, starting from distamycin A are described. One approach is based upon the selective hydrolysis via imide activation of the C-terminus amide. Besides employing traditional solution-phase synthesis, the convenient use of a polymer-supported reagent is also discussed. The other one is based upon the Curtius rearrangement of the C-terminus side chain of a convenient intermediate, easily prepared in two steps by straightforward functional group manipulation of distamycin A. Graphic
ISSN:0040-4039
1873-3581
DOI:10.1016/S0040-4039(02)01733-1