83024-11-7

Upstream product

• 142841-59-6 (2S,5S)-N-<(benzyloxy)carbonyl>-2-(4-hydroxypentyl)-5-butylpyrrolidine 
• 142925-66-4 (2S,5S)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-hydroxybutyl)pyrrolidine 
• 142925-67-5 (2S,5S)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxobutyl)pyrrolidine 
• 142841-63-2 (5R,8R)-1,12-bis(benzoyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-dodecanol 
• 142841-64-3 (5R,8R)-1-(benzoyloxy)-12-bromo-5,8-bis<(tert-butyldimethylsilyl)oxy>dodecane 
• 142841-62-1 (5R,8R)-12-(benzoyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>-1-dodecanol 
• 142841-65-4 (5R,8R)-1-(benzoyloxy)-5,8-bis<(tert-butyldimethylsilyl)oxy>dodecane 
• 142841-70-1 (2S,5S)-N-<(benzyloxy)carbonyl>-2-<4-(benzoyloxy)butyl>-5-butylpyrrolidine 
• 142841-67-6 (5R,8R)-1-(benzoyloxy)-5,8-dodecanediol cyclic sulfate 
• 142841-66-5 (5R,8R)-1-(benzoyloxy)-5,8-dodecanediol 
• 142841-69-8 (2S,5S)-2-<4-(benzoyloxy)butyl>-5-butylpyrrolidine 
• 131618-30-9 (5R,8R)-5,8-Bis<(tert-butyldimethylsilyl)oxy>-1,12-dodecanediol 
• 142841-61-0 (2S,5S)-N-<(benzyloxy)carbonyl>-5-butyl-2-(4-oxoheptyl)pyrrolidine 
• 72049-64-0 (2R,5R)-2-(4-Bromo-heptyl)-5-butyl-2,5-dihydro-pyrrole-1-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Indolizine Alkaloid Synthesis. Preparation of the Pharaoh Ant Trail Pheromone and Gephyrotoxin 223 Stereoisomers

A stereoselective entry into the 3,5-dialkylindolizidine alkaloid skeleton proceeding via N1-C2 vicinal annulation of a 1,4-dibromoalkane onto a pyrroline system is described.

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.