151024-14-5Relevant articles and documents
A synthetic approach to the phorboxazoles—synthesis of the exocyclic fragment
Leahy, James W.,Brzezinski, Linda Joy
, p. 4670 - 4672 (2016)
A strategy for the total synthesis of the phorboxazoles, including the synthesis of the exocyclic fragment corresponding to the C33–C41 portion, is reported. The primary objective was to utilize a chelation-controlled addition to an α-alkoxyaldehyde to install the oxygen atom at the C38 position.
ARYLOXYACETYLINDOLES AND ANALOGS AS ANTIBIOTIC TOLERANCE INHIBITORS
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Paragraph 0487, (2016/08/10)
The disclosure provides compounds and pharmaceutical compositions of aryloxyacetylindoles compounds and analogs useful for treating chronic and acute bacterial infections. Certain of the compounds are compounds of general Formula (I) (I) or a pharmaceutically acceptable salt or prodrug thereof. Certain compounds of this disclosure are MvfR inhibitors. MvfR inhibitors reduce the formation of antibiotic tolerant bacterial strains and are useful for treating Gram-negative bacterial infections and reducing the virulence of Pseudomonas aeruginosa. Methods of treating bacterial infections in a subject, including Pseudomonas aeruginosa infections, are also provided by the disclosure.
A total synthesis of hydroxylysine in protected form and investigations of the reductive opening of p-methoxybenzylidene acetals
Gustafsson, Tomas,Schou, Magnus,Almqvist, Fredrik,Kihlberg, Jan
, p. 8694 - 8701 (2007/10/03)
A synthesis of (2S,5R)-5-hydoxylysine, based on (R)-malic acid and Williams glycine template as chiral precursors, has been developed. This afforded hydroxylysine, suitably protected for direct use in peptide synthesis, in 32% yield over the 13-step sequence. Regioselective reductive opening of a p-methoxybenzylidene acetal and alkylation of the Williams glycine template were key steps in the synthetic sequence. Surprisingly, the regioselectivity in opening of the p-methoxybenzylidene acetal was reversed as compared to what was expected. It was found that this was due to chelation of the trialkylsilyl choride, used as an electrophile in the reductive opening, to an adjacent azide functionality. It was also discovered that an equivalent amount of trialkylsilyl hydride was formed in the reaction, a finding that led to additional mechanistic insight into reductive openings of p-methoxybenzylidene acetals with sodium cyanoborohydride as reducing agent.
Toward a total synthesis of an aglycone of spiramycin; a chiron approach to the C-1/C-4 and the C-13/C-15 fragments
Breullles,Oddon,Uguen
, p. 6607 - 6610 (2007/10/03)
Acetalisation of p-anisaldehyde by either (R) or (S)-butanetriol has been shown to occur selectively and quantitatively by using Noyori's protocol. The crystalline dioxane derivatives R-6a and S-6a which formed respectively in these conditions have been converted efficiently into the title fragments of spiramycin.
Biocatalytic synthesis of chiral polyoxygenated compounds: Modulation of the selectivity upon changes in the experimental conditions
Herradon,Valverde
, p. 1479 - 1500 (2007/10/02)
Derivatives of both enantiomers of butane-1,2,4-triol have been obtained through a transesterification reaction catalyzed by Pseudomonas fluorescens lipase (PFL) in organic solvents. The influence of the solvent on the enantioselectivity has been thorough
Regio- and enantioselective esterifications of polyoxygenated compounds catalyzed by lipases
Herradon,Cueto,Morcuende,Valverde
, p. 845 - 864 (2007/10/02)
The lipase catalyzed esterifications of derivatives of propane-1,2,3-triol and butane 1,2,4-triol in organic solvents have been studied. The influence of several factors (lipase source, organic solvent, additives and structural variations in the substrate
