51207-70-6

Upstream product

• 1148-11-4 N-Benzyloxycarbonyl-L-proline 
• 147-85-3 L-proline 
• 221072-58-8 (2S)-benzyl 2-(1-hydroxyethyl)-1-pyrrolidinecarboxylate 
• 75315-63-8 N-(benzyloxycarbonyl)succinimide 
• 71461-30-8 (S)-2-formylpyrrolidine-1-carboxylic acid benzyl ester 
• 6216-63-3 N-Cbz-Prolinol 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 51207-68-2 (2S)-N-Benzyloxycarbony-2-(1'-hydroxy-1'-methylethyl)pyrrolidine 
• 2577-48-2 methyl (2S)-pyrrolidine carboxylate 

Downstream Products

• 90246-49-4 (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<6-oxo-2(R),5-dimethyl-7(R)-(tert-butyldiphenylsiloxy)-4(E)-octenylidene>octahydroindolizidine 
• 90246-44-9 (1S ,7aS)-tetrahydro-1-methyl-1-<6-(benzyloxy)-4(R)-methyl-2-(trimethylsilyl)-2(Z)-hexenyl>-1H,3H-pyrrolo<1,2-c>oxazol-3-one 
• 90246-46-1 (1S,7aS)-1-((Z)-(R)-6-Benzyloxy-4-methyl-2-trimethylsilanyl-hex-2-enyl)-1-methyl-tetrahydro-pyrrolo[1,2-c]oxazole 
• 90246-45-0 (8S,8aS)-8-hydroxy-8-methyl-6(Z)-<4-(benzyloxy)-2(R)-methylbutylidene>octahydroindolizidine 
• 67016-65-3 Pumiliotoxin B 
• 182001-13-4 [(S)-2-((1R,2R,5R)-1-Benzyloxy-2-hydroxy-1,5-dimethyl-non-3-ynyl)-pyrrolidin-1-yl]-acetonitrile 
• 182001-29-2 (7R,8R,8aS)-8-Benzyloxy-6-[(R)-1-iodo-2-methyl-hex-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol 
• 182000-60-8 [(S)-2-((1R,2R)-1-Benzyloxy-2-hydroxy-1-methyl-oct-3-ynyl)-pyrrolidin-1-yl]-acetonitrile 
• 182001-21-4 (3R,4R,4aS)-4-Benzyloxy-4-methyl-3-((R)-3-methyl-hept-1-ynyl)-hexahydro-pyrrolo[1,2-c][1,3]oxazine 
• 182000-74-4 (7R,8R,8aS)-8-Benzyloxy-6-[1-iodo-pent-(Z)-ylidene]-8-methyl-octahydro-indolizin-7-ol 
• 182000-81-3 (3R,4R,4aS)-4-Benzyloxy-3-hex-1-ynyl-4-methyl-hexahydro-pyrrolo[1,2-c][1,3]oxazine 
• 153108-88-4 (7S,8R,8aS)-8-(benzyloxy)-7-hydroxy-8-methyl-6-(E)-<(2R)-2-methylpentylidene>octahydroindolizidine 
• 144735-40-0 (2S)-2-<(R)-1-(benzyloxy)-1-(dimethoxymethyl)ethyl>-N-(cyanomethyl)pyrrolidine 

Relevant academic research and scientific papers

A novel approach to the enantioselective formal synthesis of pumiliotoxin 251D

An efficient enantioselective synthesis of the indolizidine framework 9 of pumiliotoxin 251D in good yield by using a Lewis acid (cat.)-promoted diastereoselective addition of ethyl lithiopropiolate to ketone 7 derived from L-proline as a key step is reported. Hydrogenation of the addition product 8a gave the desired lactam 9. At the same time the 8-epimer of 9 was synthesized for the first time.

Unexpected diastereoselectivity in AD of an L-proline-derived 1,1- disubstituted alkene

Asymmetric dihydroxylation of the L-proline-derived 1,1-disubstituted alkene 5 catalysed by either (DHQ)2PHAL or (DHQD)2PHAL unexpectedly leads to preference for the same diastereomer 7, both reactions proceeding with apparently matching double diastereoselectivity. In contrast, AD using the analogous (DHQ)2PYR or (DHQD)2PYR ligands leads to preferences for diols 7 or 8 respectively.