1015779-41-5Relevant articles and documents
Vibralactone as a tool to study the activity and structure of the ClpP1P2 complex from listeria monocytogenes
Zeiler, Evelyn,Braun, Nathalie,Boettcher, Thomas,Kastenmueller, Andreas,Weinkauf, Sevil,Sieber, Stephan A.
, p. 11001 - 11004 (2011)
The Clp proteolytic machinery has important functions in many bacteria such as L. monocytogenes. Some organisms encode for two uncharacterized ClpP isoforms. Vibralactone was used to study the activity and assembly of ClpP1 and ClpP2 subunits in a hetero-
Synthesis of (±)-vibralactone
Zhou, Quan,Snider, Barry B.
supporting information; experimental part, p. 1401 - 1404 (2009/04/12)
(Chemical Equation Presented) Reductive alkylation of methyl 2-methoxybenzoate with prenyl bromide and hydrolysis afforded methyl 6-oxo-1-prenyl-2-cyclohexenecarboxylate. Reduction of the ketone, hydrolysis, iodolactonization, ozonolysis, and intramolecular aldol reaction provided a spiro lactone cyclopentenal. Retro-iodolactonization with activated Zn, formation of the β-lactone, and reduction of the aldehyde completed an efficient first synthesis of (±)-vibralactone. No protecting groups were used except for the novel use of an iodolactone to protect both the prenyl double bond and carboxylic acid.
