131722-87-7

Upstream product

• 131722-84-4 (5S,6S,7S)-7-Acetoxy-5-(benzyloxy)-1-azabicyclo<4.3.0>non-3-en-2-one 
• 123190-73-8 Acetic acid (1S,6R,7R,8R,8aR)-6-acetoxy-8-benzyloxy-7-bromo-5-oxo-octahydro-indolizin-1-yl ester 
• 123190-64-7 Acetic acid (3R,3aR,6aS)-3-benzyloxy-4-(2-chloro-acetyl)-hexahydro-furo[3,2-b]pyrrol-2-yl ester 

Downstream Products

• 131722-88-8 (1S,6R,7S,8R,8aS)-8-(Benzyloxy)-1,6,7-triacetoxyoctahydroindolizidin-5-one 
• 131635-70-6 (1S,7R,8R,8aR)-8-(Benzyloxy)-1,7-dihydroxyoctahydroindolizidine 
• 79831-76-8 (1S,6S,7R,8R,8aR)-2,6,7,8-tetrahydroxy-indolizidine 
• 131635-72-8 (1S,6S,7S,8R,8aR)-8-(Benzyloxy)-6-fluoro-1,7-dihydroxyoctahydroindolizidine 
• 131635-71-7 (1S,6R,7S,8R,8aR)-1,7-Diacetoxy-8-(benzyloxy)-6-fluorooctahydro-5-indolizidin-5-one 
• 131722-89-9 (1S,6S,7R,8R,8aR)-8-(Benzyloxy)-1,6,7-trihydroxyoctahydroindolizidine 
• 123190-77-2 (1R,6R,7S,8S,8aS)-8-Benzyloxy-octahydro-indolizine-1,6,7-triol 
• 123190-76-1 Acetic acid (1R,6S,7R,8S,8aS)-6,7-diacetoxy-8-benzyloxy-5-oxo-octahydro-indolizin-1-yl ester 
• 79831-76-8 (+/-)-castanospermin 

Relevant academic research and scientific papers

Total, Asymmetric Synthesis of (+)-Castanospermine, (+)-6-Deoxycastanospermine, and (+)-6-Deoxy-6-fluorocastanospermine

Bromination of the dibenzyl acetal of (-)-(1S,4S)-7-oxabicyclohept-5-en-2-one ((-)-5) led to (+)-(1S,5S,6S,7S)-6-endo-(benzyloxy)-5-exo-bromo-7-oxabicycloheptan-2-one (25).Baeyer-Villiger oxidation of 25 gave 2-O-benzyl-3-bromo-3,5-dideoxy-β

A HIGHLY STEREOSELECTIVE TOTAL SYNTHESIS OF (+/-)CASTANOSPERMINE

An efficient synthesis of (+/-)castanospermine based on the bromine addition to 7-oxabicyclohept-5-en-2-one benzyl acetal is presented.