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Elaboration of vinblastine hybrids using a reactive in situ generated N-carboxyanhydride

Organic and Biomolecular Chemistry, ISSN: 1477-0520, Vol: 9, Issue: 13, Page: 4873-4881
2011
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Hybrids of vinblastine and phomopsin, designed by a molecular modelling study, were elaborated in order to target tubulin. The key step of the synthesis (fragmentation and insertion of vindoline) was mediated by an internal N-carboxyanhydride (or O-acylcarbamate). This reaction was diastereospecific and addition of silver salts could reverse the diastereoselectivity. Even if the synthesized compounds are inactive, this synthesis represents an original example of a C-N fragmentation mediated by a N-carboxyanhydride. © The Royal Society of Chemistry 2011.

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