365449-54-3

Upstream product

• 98-59-9 p-toluenesulfonyl chloride 
• 7480-35-5 (1S,2R)-1-amino-2-indanol 
• 591-80-0 pent-4-enoic acid 
• 171562-32-6 N-((1S,2R)-2-hydroxy-2,3-dihydro-1H-inden-1-yl)-4-methylbenzenesulfonamide 

Downstream Products

• 540770-25-0 (2S,1'S)-2-(2'-benzyloxy-1'-hydroxyethyl)pent-4-enoic acid 
• 365449-55-4 (2S,1'S,1S,2R)-1-p-tosylaminoindan-2-yl 2-(2'-benzyloxy-1'-hydroxyethyl)pent-4-enoate 

Relevant academic research and scientific papers

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

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.

Asymmetric total synthesis of the gastroprotective microbial agent AI-77-B

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.

[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