871706-30-8Relevant academic research and scientific papers
Inhibition of quorum sensing and biofilm formation in Vibrio harveyi by 4-fluoro-DPD; A novel potent inhibitor of AI-2 signalling
Kadirvel, Manikandan,Fanimarvasti, Fariba,Forbes, Sarah,McBain, Andrew,Gardiner, John M.,Brown, Gavin D.,Freeman, Sally
supporting information, p. 5000 - 5002 (2014/05/06)
(S)-4,5-Dihydroxypentane-2,3-dione [(S)-DPD, (1)] is a precursor for AI-2, a quorum sensing signalling molecule for inter- and intra-species bacterial communication. The synthesis of its fluoro-analogue, 4-fluoro-5-hydroxypentane- 2,3-dione (2) is reported. An intermediate in this route also enables a new, shorter synthesis of the native (S)-DPD. 4-Fluoro-DPD (2) completely inhibited bioluminescence and bacterial growth of Vibrio harveyi BB170 strain at 12.5 μM and 100 μM, respectively.
Diastereodivergent synthesis of trisubstituted alkenes through protodeboronation of allylic boronic esters: Application to the synthesis of the californian red scale beetle pheromone
Hesse, Matthew J.,Butts, Craig P.,Willis, Christine L.,Aggarwal, Varinder K.
supporting information, p. 12444 - 12448 (2013/02/23)
E-allylic boronic esters undergo a highly diastereoselective protodeboronation with TBAF·3 H2O to give Z-trisubstituted alkenes. The selectivity can be switched to give predominantly the E-alkene instead by using KHF2/TsOH (see scheme). The utility of the methodology has been illustrated in a short synthesis of a component of the sex pheromone of the Californian red scale beetle. Copyright
O-directed free-radical hydrostannations of propargyl ethers, acetals, and alcohols with Ph3SnH and Et3B
Dimopoulos, Paschalis,Athlan, Audrey,Manaviazar, Soraya,George, Jonathan,Walters, Marcus,Lazarides, Linos,Aliev, Abil E.,Hale, Karl J.
, p. 5369 - 5372 (2007/10/03)
(Chemical Equation Presented) The O-directed hydrostannation of various propargyloxy substrates is reported with Ph3SnH/Et3B.
First total synthesis of the marine illudalane sesquiterpenoid alcyopterosin E.
Witulski, Bernhard,Zimmermann, Axel,Gowans, Nicholas D
, p. 2984 - 2985 (2007/10/03)
The first synthesis of the marine illudalane sesquiterpenoid alcyopterosin E was accomplished through a concise ABC ring-formation strategy using a rhodium(I)-catalysed intramolecular alkyne cyclotrimerisation as key connection.
Palladium catalyzed cyclizations of enantiomerically pure acyclic 4-acetoxy-2,8-nonadienes: Efficient chirality transfer
Oppolzer, Wolfgang,Birkinshaw, Timothy N.,Bernardinelli, Gerald
, p. 6995 - 6998 (2007/10/02)
S-4-Acetoxy-6-aza-2,8-nonadienes 9 and 11 were subjected to Pd(0)-catalyzed cyclizations. The S,E-acetate 9 gave exclusively S,E-pyrrolidine 12, whereas the antipodal product R,E-12 was formed from the S,Z-precursor 11 (Scheme 3). X-ray-diffraction analys
