765-27-5Relevant articles and documents
The synthesis of methyl 4-(2-octadecylpropen-1-yl)butanoate: a possible inhibitor in mycolic acid biosynthesis
Besra, Gurdyal S.,Minnikin, David E.,Simpson, Michael J.,Baird, Mark S.,Wheeler, Paul R.,Ratledge, Colin
, p. 35 - 40 (1993)
The high molecular weight 2-alkyl-3-hydroxy mycolic acids are key structural components of the cell envelope of pathogenic mycobacteria such as Mycobacterium tuberculosis.It has been shown recently that (Z)-tetracos-5-enoic acid is a key initial intermediate in mycolic acid biosynthesis in extracs of Mycobacterium smegmatis.This acid is presumably formed by desaturation of tetracosanoate, and previous studies on oleic acid biosynthesis suggest that a cycloproene analogue may be a potential inhibitor.This communication describes the synthesis of methyl 4-(2-octadecylcyclopropen-1-yl)butanoate, which is shown elsewhere to be an inhibitor of the initial stages of mycolic acid synthesis. Key words: Mycobacteria; Mycolic acids; Cyclopropene fatty acid; Biosynthetic inhibitor
Synthesis of elenic acid, an inhibitor of topoisomerase II
Hoye,Baigorria,Danielson,Pragman,Rajapakse
, p. 2450 - 2453 (2007/10/03)
A short, efficient synthesis of elenic acid, a marine natural product with interesting biological activity, has been completed. Critical features of the synthesis are the development of methodology for the one-pot elaboration of an alkyne to an (E)-β,γ-unsaturated ester with a stereocenter at the α-position and the use of the zipper reaction of a 1- arylalkyne. This reaction has not been previously reported with aromatic substrates. The synthesis strategy provides considerable flexibility for the preparation of structural analogues.
IMPROVED NUCLEOPHILIC DISPLACEMENTS IN N-METHYL PYRROLIDINONE AS A SOLVENT
Tyman, John,Ghorbanian, Shoreh,Muir, M.,Tychopoulous, Vasiliki,Bruce, Ian,Fisher, Ian
, p. 179 - 188 (2007/10/02)
The nucleophilic displacement reactions of 2- and 4-halogenonaphthalic-1,8-anhydrides and the N-imides, of 4,7-dichloroquinolines, the alkylation of lithio alkynes, the methylation of ethyl or methyl diacetylacetate and a variety of related reactions are greatly facilitated in N-methylpyrrolidinone as aprotic solvent.
