- A stereoselective anti-aldol route to (3R,3aS,6aR)-hexahydrofuro[2,3-b] furan-3-ol: A key ligand for a new generation of HIV protease inhibitors
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A stereoselective synthesis of (3R,3aS,6aR)-hexahydrofuro[2,3-b]furan-3-ol, an important high affinity P2-ligand, in high enantiomeric excess (>99%) is reported. The synthesis features an ester-derived titanium enolate based highly stereoselective anti-aldol reaction as the key step. Georg Thieme Verlag Stuttgart.
- Ghosh, Arun K.,Li, Jianfeng,Perali, Ramu Sridhar
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p. 3015 - 3018
(2008/02/08)
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- Asymmetric total synthesis of the gastroprotective microbial agent AI-77-B
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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).
- Ghosh, Arun K.,Bischoff, Alexander,Cappiello, John
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p. 821 - 832
(2007/10/03)
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- Stereoselective synthesis of pseudopeptide microbial agent AI-77-B.
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[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
- Ghosh,Bischoff,Cappiello
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p. 2677 - 2680
(2007/10/03)
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