Described herein are certain boron-containing compounds, compositions, preparations and their use as modulators of the transpeptidase function of bacterial penicillin-binding proteins and as antibacterial agents. In some embodiments, the compounds described herein inhibit penicillin-binding proteins. In certain embodiments, the compounds described herein are useful in the treatment of bacterial infections.
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Paragraph 00295
(2018/12/13)
A Concise Enantioselective Total Synthesis of (?)-Virosaine A
The total synthesis of (?)-virosaine A (1) was achieved in ten steps starting from furan and 2-bromoacrolein. A one-pot Diels–Alder cycloaddition/organolithium addition initiated an efficient sequence to access a key oxime/epoxide intermediate. Heating this intermediate in acetic acid resulted in an intramolecular epoxide opening/nitrone [3+2] cycloaddition cascade to construct the caged core of 1 in a single step. Several methods of C?H functionalization were assessed on the cascade product, and ultimately, a directed lithiation/bromination effected selective C14 functionalization, enabling the synthesis of 1.
Hughes, Jonathan M. E.,Gleason, James L.
supporting information
p. 10830 - 10834
(2017/08/30)
O-TBS-N-tosylhydroxylamine: A reagent for facile conversion of alcohols to oximes
(Chemical Equation Presented) A variety of oximes were synthesized from the corresponding alcohols, alkyl halides, or alkyl sulfonates without using external oxidants. With this simple two-step procedure involving substitution with readily available TsNHOTBS and subsequent treatment with CsF, a range of oximes were prepared including the ones hardly preparable with conventional procedures.
Synthetic methodology for the preparation of N-hydroxysulfamides
A convenient synthesis of a variety of substituted N-hydroxysulfamides from chlorosulfonyl isocyanate is reported. Alkyl groups can be introduced selectively on the N-Boc nitrogen of key intermediates 1a or 1b using the Mitsunobu reaction with alcohols. S
Devanathan, Krishnaswamy,Bell, Jennifer A.,Wilkins, Patricia C.,Jacobs, Hollie K.,Gopalan, Aravamudan S.
p. 8029 - 8033
(2008/03/18)
New C-3′ hydroxamate-substituted and more lipophilic cyclic hydroxamate cephalosporin derivatives as a potential new generation of selective antimicrobial agents
Syntheses of a series of new C-3′ hydroxamate-substituted cephalosporin derivatives with potent antibacterial and media-dependent anti-TB activity are described. The Royal Society of Chemistry 2006.