Tetrahydro-1-methyl-3,3-diphenyl-1H, 3H-pyrrolo[1,2-c][1,3,2]oxazaborole

Mathre, David J.; Shinkai, I.; Zaidlewicz, M.; Krzemiński, M.; Łączkowski, Krzysztof Z.; Patti, Angela; Pedotti, Sonia

doi:10.1002/047084289x.rt035s.pub3

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“…If one considers the relationship between alnustone (1) and ( R) -2 or ( S) -2, it can be readily seen that ( R) -2 and ( S) -2 could be obtained from enantioselective reduction of the carbonyl group of alnustone (1). Chiral oxazaborolidines have been used as reagents or catalysts (with borane sources) for enantioselective reduction of prochiral ketones [26]. In this manner, Corey et al [27] efficiently used ( S) -2-methyl-CBS-oxazaborolidine as a catalyst with BH 3 in the enantioselective reduction of aryl ketones to give the corresponding chiral alcohols with predominant R configuration (ee~84-96.7%).…”

Section: Resultsmentioning

confidence: 99%

Syntheses and antibacterial activities of 4 linear nonphenolic diarylheptanoids

et al. 2020

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Four linear nonphenolic diarylheptanoids were synthesized and their antibacterial activities were studied. (S)-2-Me-CBS-catalysed reduction of alnustone with BH 3 .SMe 2 gave (R) (-)(4 E ,6 E)-1,7-diphenylhepta-4,6-dien-3-ol, a natural product. Reduction of alnustone with Na in t-BuOH at-15°C under NH 3 atm gave (E)-1,7-diphenylhept-5en-3-one as a Birch-type reduction product. t-BuOK catalysed condensation of benzalacetone with propionyl chloride gave (4 Z ,6 E)-5-hydroxy-1,7-diphenylhepta-4,6-dien-3-one, a natural product. (1 E ,4 Z ,6 E)-5-Hydroxy-4-phenethyl-1,7-diphenylhepta-1,4,6-trien-3-one, a curcuminoid, was synthesized starting from pentan-2,4-dione in 3 steps. The synthesized chemical compounds were applied against 2 gram-positive bacteria (Bacillus cereus and Arthrobacter agilis), 4 gram-negative bacteria (Pseudomonas aeruginosa, Xanthomonas campestris, Klebsiella oxytoca, and Helicobacter pylori), and 1 yeast (Candida albicans) by the disc diffusion method. All of the synthesized compound exhibited different degrees of antimicrobial activity at concentrations between 20-100 µg/disc against the test organisms.

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Section: Resultsmentioning

confidence: 99%