Diastereoselective reduction of cyclic bioactive Mannich ketones

Tamás Lóránd, Erzsébet Osz, Gyula Kispál, Gergely Nagy, Edgar Weckert, Daniel Luebbert, Alke Meents, Béla Kocsis, László Prókai

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

The reduction of cyclic Mannich ketones having antibacterial activity showed poor stereoselectivity with L-Selectride®, sodium trimethoxyborohydride and diisobutylaluminium hydride, while lithium aluminium hydride and, in particular, sodium borohydride often yielded a single stereoisomer. The size of the ring strongly influenced the stereocomposition of the reaction mixtures. An increased preference for the trans isomer was attributed to a weak intramolecular hydrogen bond between the OH and the N, as demonstrated by X-ray crystallography. After reduction, the antibacterial activity of the product decreased dramatically ("S-form") but was not completely abolished in deep rough mutants of Gram-negative bacteria.

Original languageEnglish
Pages (from-to)34-52
Number of pages19
JournalArkivoc
Volume2004
Issue number7
StatePublished - 1 Jan 2004

Keywords

  • Deep rough (Re) mutants
  • Molecular modelling
  • NMR spectroscopy
  • Reduction
  • X-ray crystallography

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