124662-61-9Relevant academic research and scientific papers
Diastereoselective Alkene Hydroesterification Enabling the Synthesis of Chiral Fused Bicyclic Lactones
Shi, Zhanglin,Shen, Chaoren,Dong, Kaiwu
supporting information, p. 18039 - 18042 (2021/11/16)
Palladium-catalysed diastereoselective hydroesterification of alkenes assisted by the coordinative hydroxyl group in the substrate afforded a variety of chiral γ-butyrolactones bearing two stereocenters. Employing the carbonylation-lactonization products as the key intermediates, the route from the alkenes with single chiral center to chiral THF-fused bicyclic γ-lactones containing three stereocenters was developed.
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.
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 and absolute configuration of the 7-phenylhepta-4,6-diyne-1,2- diol isolated from Bidens pilosa
Cui, Shan,Zou, Yang,Wu, Yikang,Gao, Po
scheme or table, p. 2131 - 2135 (2011/08/04)
The title diynediol was synthesized in enantiopure (>98.4% ee) forms, with the cross coupling of phenylacetylene with either (R)- or (S)-5-benzyloxypent-1-yn-4-ol catalyzed by nickel(II) chloride-copper(I) iodide as the key step. Comparison of the spectro
First stereoselective synthesis of synargentolide A and revision of absolute stereochemistry
Sabitha, Gowravaram,Gopal, Peddabuddi,Reddy, C. Nagendra,Yadav
scheme or table, p. 6298 - 6302 (2010/01/18)
The first stereoselective total synthesis of synargentolide A isolated from Syncolostemon argenteus has been achieved from commercially available (R)-benzyl glycidyl ether using Sharpless asymmetric epoxidation and cross-metathesis reactions as the key st
Double conjugate addition of dithiols to propargylic carbonyl systems to generate protected 1,3-dicarbonyl compounds
Sneddon, Helen F.,Van Den Heuvel, Alexandra,Hirsch, Anna K. H.,Booth, Richard A.,Shaw, David M.,Gaunt, Matthew J.,Ley, Steven V.
, p. 2715 - 2725 (2007/10/03)
The work describes the efficient double conjugate addition of ethane and propane dithiols in the presence of sodium methoxide to a wide variety of propargylic carbonyl containing compounds. The products of these reactions are differentiated, 1,3-dicarbony
Chemical variation of natural product-like scaffolds: Design and synthesis of spiroketal derivatives
Zinzalla, Giovanna,Milroy, Lech-Gustav,Ley, Steven V.
, p. 1977 - 2002 (2008/02/04)
The design and synthesis of spiroketal structures and their chemical modification, leading to a collection of new small molecules for biological evaluation as orally-bioavailable lead compounds is described. Both [6,5]- and [6,6]-membered ring spiroketal units have been prepared in a stereochemically-varying fashion starting from commercially available (R)- or (S)-glycidol, in ten, eleven and twelve linear steps, in overall yields of 45, 40 and 20%, respectively. Further elaboration according to Lipinski's guidelines has given a collection of structurally-diverse, new spiroketal derivatives in high yields and with high purity. The Royal Society of Chemistry 2006.
A Concise Enantiocontrolled Route to (+)-Patulolide C
Takano, Seiichi,Murakami, Taku,Samizu, Kiyohiro,Ogasawara, Kunio
, p. 67 - 72 (2007/10/02)
A naturally occurring antifungal macrolide (+)-patulolide C has been synthesized enantioselectively via the C2-symmetric bis-epoxide by incorporation of two molecular units of (R)-O-benzylglycidol.
Synthesis of (Z)-Homoallylic Alcohols and Homoprop-2-ynylic Alcohols via Palladium-catalysed Hydrogenolysis of Prop-2-ynylic Cyclic Carbonates
Kang, Suk-Ku,Park, Dong-Chul,Cho, Dong-Gyu,Chung, Jea-Uk,Jung, Kyung-Yun
, p. 237 - 238 (2007/10/02)
The decarboxylation-hydrogenolysis of prop-2-ynylic cyclic carbonates which have an internal acetylenic bond with ammonium formate in the presence of a catalytic amount of and Bu3nP afforded (Z)-homoallylic alcohols or homoprop-2-yn
6-membered lactones useful as intermediates for antilipemic mevalonic acid lactones
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, (2008/06/13)
A compound of the formula: STR1 wherein R is an unsubstituted benzyl group, a p-nitrobenzyl group, a benzyl group in which the phenyl group is substituted by one or two substituents selected from the group consisting of C1 -C4 alkyl
