Ghosh, Arun K. published the artcileAsymmetric total synthesis of the gastroprotective microbial agent AI-77-B, Recommanded Product: Methyl 4,4,4-trichlorobutanoate, the main research area is gastroprotective pseudopeptide microbial agent AI77B asym total synthesis dihydroisocoumarin; coumarin dihydroiso condensation hydroxy amino acid; leucinal stereoselective alkylation alkynyl ester methoxycyclohexadiene regioselective Diels Alder; aldol reaction Curtius rearrangement homologation; AI-77-B; Asymmetric synthesis; Natural products; Total synthesis.
An enantioselective total synthesis of the pseudopeptide microbial agent AI-77-B, which has shown potent antiulcerogenic properties, is described. The synthesis is convergent and involves the assembly of a dihydroisocoumarin fragment and a hydroxy amino acid. The dihydroisocoumarin derivative was synthesized by means of a Diels-Alder reaction between 1-methoxy-1,3-cyclohexadiene and an alkynyl ester derivative as the dienophile. The alkynyl ester was obtained stereo-selectively by two different synthetic routes: (1) A stereoselective alkylation of leucinal, and (2) a titanium enolate-mediated anti-aldol reaction with trichlorobutyraldehyde, a novel homopropargylaldehyde equivalent The stereocenters of the hydroxy amino acid moiety were generated through a titanium enolate-mediated syn-aldol reaction, Curtius rearrangement, and application of Dondoni’s aldehyde homologation. Condensation of the dihydroisocoumarin and hydroxy amino acid moieties and subsequent removal of the protecting groups furnished optically active AI-77-B.
European Journal of Organic Chemistry published new progress about Aldol condensation, stereoselective. 19376-57-9 belongs to class chlorides-buliding-blocks, name is Methyl 4,4,4-trichlorobutanoate, and the molecular formula is C5H7Cl3O2, Recommanded Product: Methyl 4,4,4-trichlorobutanoate.
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