113276-96-3Relevant academic research and scientific papers
Synthesis of the β-lactone esterase inhibitor valilactone using πallyltricarbonyliron lactone complexes
Bates, Roderick W.,Fernandez-Moro, Rosalina,Ley, Steven V.
, p. 2651 - 2654 (1991)
Synthesis of the esterase inhibitor valilactone (1) is reported employing the oxidation of π-allyltricarbonyliron lactone complexes with ceric ammonium nitrate to afford the inherent β-lactone ring.
Asymmetric synthesis of valilactone
Mineeva
, p. 100 - 104 (2014)
Total synthesis of (-)-valilactone, an efficient pancreatic lipase inhibitor, was accomplished with the use of Keck allylation in the key step of construction of the target carbon skeleton.
BETA-LACTONE COMPOUNDS
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Page/Page column 21; 42, (2009/05/28)
The present invention provides compounds having the general structure A, or a pharmaceutically acceptable derivatives thereof: wherein R is an alkyl group, and R1 comprises at least one moiety selected from a group consisting of an alkyl, an alkenyl, an aryl, a heterocycle, hydroxyl, ester, amido, aldehyde, and a halogen.
Asymmetric synthesis of tetrahydrolipstatin and valilactone
Case-Green, Stephen C.,Davies, Stephen G.,Roberts, Paul M.,Russell, Angela J.,Thomson, James E.
experimental part, p. 2620 - 2631 (2009/04/06)
The highly diastereoselective aldol reaction between acyl complexes of the iron chiral auxiliary [(η5-C5H5)Fe(CO)(PPh3)] and β-hydroxy aldehydes (obtained via a Noyori asymmetric hydrogenation), followed by a tandem oxidative decomplexation-cyclisation process gives access to β-substituted and α,β-disubstituted β-lactones in high ee. This methodology has been employed in the asymmetric syntheses of tetrahydrolipstatin and valilactone.
Total synthesis and comparative analysis of orlistat, valilactone, and a transposed orlistat derivative: Inhibitors of fatty acid synthase
Ma, Gil,Zancanella, Manuel,Oyola, Yatsandra,Richardson, Robyn D.,Smith, Jeffrey W.,Romo, Daniel
, p. 4497 - 4500 (2007/10/03)
Concise syntheses of orlistat (Xenical), a two-carbon transposed orlistat derivative, and valilactone are described that employ the tandem Mukaiyama aldol-lactonization (TMAL) process as a key step. This process allows facile modification of the α-side chain. Versatile strategies for modifying the δ-side chain are described, involving cuprate addition and olefin metathesis. Comparative antagonistic activity of these derivatives toward a recombinant form of the thioesterase domain of fatty acid synthase is reported along with comparative activity-based profiling.
An expeditious enantioselective total synthesis of valilactone
Wu, Yikang,Sun, Ya-Ping
, p. 5748 - 5751 (2007/10/03)
The title compound was synthesized through an expeditious route using Crimmins aldolization to establish the two key stereogenic centers and a hydroxyl group activation (HGA) protocol to construct the anti α,β-disubstituted β-lactone from the corresponding syn aldol.
