142841-61-0

Upstream product

• 142841-60-9 (2R,5R)-N-<(benzyloxy)carbonyl>-2-(4-hydroxyheptyl)-5-butylpyrrolidine 
• 162335-17-3 (2R,5S)-2-Butyl-5-((E)-4-oxo-hept-2-enyl)-pyrrolidine-1-carboxylic acid benzyl ester 
• 54313-25-6 4-penten-1-yllithium 
• 5211-23-4 N-carbobenzyloxy-L-proline methyl ester 
• 214072-10-3 (5S)-2-Methoxy-1-[(benzyloxy)carbonyl]-5-methoxycarbonylpyrrolidine 
• 1119-51-3 bromopentene 
• 158149-94-1 (2S,5S)-1-[(Benzyloxy)carbonyl]-2-hydroxymethyl-5-(pent-4-enyl)pyrrolidine 
• 158250-28-3 (2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(pent-4-enyl)pyrrolidine 
• 158149-95-2 (2S,5R)-1-[(Benzyloxy)carbonyl]-2-methoxycarbonyl-5-(pent-4-enyl)pyrrolidine 
• 158149-93-0 (2S,5S)-1-[(Benzyloxy)carbonyl]-2-tosyloxymethyl-5-(pent-4-enyl)pyrrolidine 
• 214072-11-4 (2R,5R)-1-[(Benzyloxy)carbonyl]-2-butyl-5-(4,5-epoxypentyl)pyrrolidine 
• 17615-01-9 1-(triphenyl-λ⁵-phosphanylidene)pentan-2-one 
• 136092-36-9 ((R)-5-Butyl-pyrrolidin-2-yl)-acetic acid methyl ester 
• 136092-37-0 (5R)-Z-Methyl (5-butyl-2-pyrrolidinylidene)acetate 

Downstream Products

• 67217-85-0 (-)-indolizidine 223AB 
• 943979-38-2 (3R,5S,8aR)-3-butyl-5-propyloctahydroindolidine 
• 67217-85-0 (3S,5R,8aS)-3-butyl-5-propyloctahydroindolidine 
• 142925-68-6 indolizidine 223AB 

Relevant academic research and scientific papers

Highly diastereoselective synthesis and NMR characterization of natural indolizidine alkaloids

A diastereoselective, general and versatile access to disubstituted indolizidines is described. The nmr conformational analysis permits us to establish preferred conformations.

Synthesis of indolizidines (-)-195B, (-)-223AB and (-)-239AB: (2S,5R)- l-[(benzyloxy)carbonyl]-2-methoxycarbonyl-5-(4pentenyl)pyrrolidine as a versatile chiral building block

The total syntheses of three levogyre 3,5-disubstituted indolizidines, (-)-195B, (-)-223AB and (-)-239AB are described. The employed strategy is based on the utilization of the common enantiopure trans 2,5-disubstituted pyrrolidine 3, which is assembled b

ENANTIOSELECTIVE SYNTHESIS OF (-)-GHEPHYROTOXINE 223AB

A highly enantioselective synthesis of the dendrobatid indolizidine alkaloid 223AB is described using a chiral amino acid as starting material.

General Entry to the 3,5-Disubstituted Indolizidine Class of Dendrobatid Alkaloids. Total Syntheses of Both Enantiomers of Indolizidines 195B, 223AB, 239AB, and 239CD from a Common Chiral Synthon

A general protocol for the total syntheses of both enantiomers of dendrobatid alkaloids, indolizidines 195B, 223AB, 239AB, and 239CD, belonging to the 3,5-disubstituted indolizidine subclass is described, in which 3,4-dideoxy-D-threo-hexitol (8) has been used as single and common chiral synthon.The syntheses of the (+)- and (-)-enantiomers of these alkaloids begin with (S,S)- and (R,R)-1,2:5,6-diepoxyhexanes (7), respectively, both of which were derived from 8 in three steps and are carried out by way of pyrrolidine formation via the cyclic sulfates leading to the(2R,5R)- and (2S,5S)-trans-2,5-dialkylated pyrrolidines, which were converted to the (+)- and (-)-enantiomers, respectively, of the title indolizidine alkaloids.These syntheses involve the first chiral preparations of indolizidines 239AB, 239CD both in natural (-)- and unnatural (+)-enantiomeric forms, which confirm the absolute configurations of natural 239AB and 239CD as 3R,5S,8aR and 3R,5R,8aR, respectively.