98362-11-9

Upstream product

• 130464-33-4 (6R,7R,8R,8aS)-6,7,8-triacetoxyindolizidine 
• 69610-41-9 Boc-L-Pro-H 
• 1228764-33-7 (6R,7R,8R,8aS)-6,7,8-tris(benzyloxy)-3,5,6,7,8,8a-hexahydroindolizine 
• 130464-32-3 (6R,7R,8R,8aR)-6,7,8-triacetoxyindolizidine 
• 198493-30-0 tert-butyl (2S)-2-(2-oxoethyl)pyrrolidine-1-carboxylate 
• 1379528-14-9 (S,Z)-tert-butyl 2-(2-(tert-butyldimethylsilyloxy)vinyl)pyrrolidine-1-carboxylate 
• 1379528-16-1 (6S,7S,8R,8aR)-5-oxooctahydroindolizine-6,7,8-triyl triacetate 
• 1379528-15-0 (6S,7S,8R,8aR)-6,7,8-trihydroxyhexahydroindolizin-5(1H)-one 
• 1379528-08-1 (3S,4S,E)-3,4-bis(tert-butyldimethylsilyloxy)-3,4,8,9-tetrahydro-1H-azonin-2(7H)-one 
• 1379528-10-5 (S,Z)-2-(tert-butyldimethylsilyloxy)-1-(2-(2-(tertbutyldimethylsilyloxy)vinyl)pyrrolidin-1-yl)ethanone 
• 130359-90-9 Methanesulfonic acid 3-((3aS,5aR,8aR,8bS)-2,2,7,7-tetramethyl-tetrahydro-bis[1,3]dioxolo[4,5-b;4',5'-d]pyran-3a-yl)-propyl ester 
• 130359-41-0 2-((1R,2S,3R)-1,2,3,4-Tetrahydroxy-butyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 130359-33-0 ethyl 3-(1,2;3,4-di-O-isopropylidene-β-D-arabinopyranosyl)propanoate 
• 130359-35-2 3-(1,2;3,4-di-O-isopropylidene-β-D-arabinopyranosyl)propyl azide 

Relevant academic research and scientific papers

Divergent total synthesis of 1,6,8a-tri-epi-castanospermine and 1-deoxy-6,8a-di-epi-castanospermine from substituted azetidin-2-one (β-lactam), involving a cascade sequence of reactions as a key step

A divergent, short, and novel total synthesis of 1,6,8a-tri-epi- castanospermine (7) and 1-deoxy-6,8a-di-epi-castanospermine (8) has been developed via a common precursor, 15, obtained from d-mannitol derived β-lactam. The key step involves a one pot cascade sequence of trimethyl sulfoxonium ylide based cyclization of epoxy sulfonamide 14via epoxide ring opening, one carbon homologation followed by intramolecular cyclization. This journal is the Partner Organisations 2014.

Asymmetric syntheses of 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine

Asymmetric syntheses of both 1-deoxy-6,8a-di-epi-castanospermine and 1-deoxy-6-epi-castanospermine, polyhydroxylated indolizidine alkaloids that act as selective glycosidase inhibitors, have been accomplished in seven steps. The key feature of our unique syntheses includes the stereoselective introduction of the C-3 and C-4 hydroxyl groups utilizing the aza-Claisen rearrangement-induced ring expansion of 1-acyl-2-alkoxyvinyl pyrrolidine and a substrate-controlled stereoselective transannulation of the resulting azoninone intermediate.

A new synthetic access to bicyclic polyhydroxylated alkaloid analogues from pyranosides

A facile, versatile and stereoselective synthesis of bicyclic polyhydroxylated alkaloids as castanospermine analogues is described. The synthetic route started from methyl pyranosides. The key steps involved a high-yielding expeditious one-pot tandem reaction from alkenes to N-substituted δ-lactams. The δ-lactams were stereoselectively vinylated to give the dienes, which were followed by the ring-closing metathesis to produce the cyclized products. The functional group transformations of the resulting bicyclic compounds furnished diverse polyhydroxylated alkaloids in good yields. The Royal Society of Chemistry 2010.

A convenient synthesis of 1-deoxy-8a-epi-castanospermine diastereoisomers (6R,7R,8S,8aS)-6,7,8-trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8trihydroxyindolizidine

An efficient synthesis of (6R,7R,8S,8aS)-6,7,8-trihydroxyindolizidine and (6R,7R,8R,8aS)-6,7,8-trihydroxyindolizidine is described from readily available N-BOC-L-proline, (BOC = tert-butoxycarbonyl) which involves the addition of ethyl lithiopropiolate to the aldehyde derived from N-BOC-L-proline as a key step, then cyclization to construct indolizidine skeletons and asymmetric dihydroxylation. Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2003.

Synthesis of 1-deoxy-6-epicastanospermine and 1-deoxy-6,8a-diepicastanospermine.

Extension of the carbon spine of 2,3;4,5-di-O-isopropylidene-beta-D-fructopyranoside by oxidation at C-1 followed by a Wittig reaction using the phosphorane Ph3P = CHCO2Et gave an oct-4-ulose derivative, which was then transformed into the key intermediat