135501-85-8Relevant 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.
The regio- and stereospecific intermolecular dehydrative alkoxylation of allylic alcohols catalyzed by a gold(I) N-heterocyclic carbene complex
Mukherjee, Paramita,Widenhoefer, Ross A.
supporting information, p. 3437 - 3444 (2013/07/05)
A 1:1 mixture of [AuCl(IPr)] (IPr=1,3-bis(2,6-diisopropylphenyl)imidazol-2- ylidine) and AgClO4 catalyzes the intermolecular dehydrative alkoxylation of primary and secondary allylic alcohols with aliphatic primary and secondary alcohols to for
Highly stereoselective C-C bond formation by rhodium-catalyzed tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor carbenoids and chiral allylic alcohols
Li, Zhanjie,Parr, Brendan T.,Davies, Huw M. L.
supporting information; experimental part, p. 10942 - 10946 (2012/08/07)
The tandem ylide formation/[2,3]-sigmatropic rearrangement between donor/acceptor rhodium carbenoids and chiral allyl alcohols is a convergent C-C bond forming process, which generates two vicinal stereogenic centers. Any of the four possible stereoisomers can be selectively synthesized by appropriate combination of the chiral catalyst Rh2(DOSP)4 and the chiral alcohol.
Synthesis of Enantioenriched α-Hydroxy-α-allenylacetic Acids by Wittig Rearrangement of (Propargyloxy)acetates
Marshall, James A.,Wang, Xiao-jun
, p. 4913 - 4918 (2007/10/02)
Optically active (R)-(propargyloxy)acetic esters 5, available in ca. 90 percent ee through reduction of alkynones 2 with Chirald-LiAlH4 followed by alkylation with chloroacetic acid and esterification with CH2N2, undergo highly stereoselective rearr
A Route to Key Fragments of Mycoticin B and Amphotericin B from (S)-O-Benzylglycidol
Takano, Seiichi,Shimazaki, Youichi,Sekiguchi, Yoshinori,Ogasawara, Kunio
, p. 2041 - 2044 (2007/10/02)
A concise enantioselective synthesis of C27-34 fragment of mycoticin B and C31-37 fragment of amphotericin B is described using a common building block prepared from (S)-O-benzylglycidol.
A Simple Preparation of Five-Carbon Chiral Allylic and Homoallylic Alcohol Synthons
Takano, Seiichi,Sekiguchi, Yoshinori,Sato, Nobuaki,Ogasawara, Kunio
, p. 139 - 141 (2007/10/02)
Five-carbon homoallylic and allylic alcohols 4, 5, and 6, potentially useful building blocks for the syntheses of a wide variety of optically active compounds, are prepared from chiral (S)-O-benzylglycidol (1) via the selective formation of the terminal a
Versatile Chiral Building Blocks bearing a Secondary Methyl Group from (S)-O-benzylglycidol (Benzyloxymethyloxirane)
Takano, Seiichi,Sekiguchi, Yoshinori,Ogasawara, Kunio
, p. 555 - 557 (2007/10/02)
Versatile chiral building blocks for the construction of chiral natural products bearing a secondary methyl group have been efficiently prepared from (S)-O-benzylglycidol.
