365449-55-4Relevant academic research and scientific papers
Synthesis of bioactive natural products by asymmetric syn-and anti-aldol reactions
Ghosh, Arun K.,Dawson, Zachary L.
scheme or table, p. 2992 - 3002 (2010/04/02)
The use of several variants of the asymmetric aldol reaction as key steps in the syntheses of bioactive target molecules is described. Georg Thieme Verlag Stuttgart.
Asymmetric total synthesis of the gastroprotective microbial agent AI-77-B
Ghosh, Arun K.,Bischoff, Alexander,Cappiello, John
, p. 821 - 832 (2007/10/03)
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 synthesised 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 stereoselectively by two different synthetic routes: (1) A stereoselective allylation of leucinal, and (2) a titanium enolate-mediated anti-aldol reaction with trichlorobutyraldehyde, a novel homopropargylaldehyde equivalent. The stereocentres 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. ( Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003).
Stereoselective synthesis of pseudopeptide microbial agent AI-77-B.
Ghosh,Bischoff,Cappiello
, p. 2677 - 2680 (2007/10/03)
[structure: see text]. An efficient and highly stereoselective synthesis of the gastroprotective natural product AI-77-B is described. The stereocenters of the hydroxy amino acid moiety were generated by an ester-derived titanium-enolate-mediated syn-aldo
