1357981-36-2

Upstream product

• 1357981-16-8 C₂₅H₂₇NO₃ 
• 1357981-31-7 (2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)-2-(4-(tert-butyldimethylsilyloxy)butyl)pyrrolidine 
• 1357981-34-0 4-[(2S,3S,4R)-1-benzyl-3,4-bis(benzyloxy)pyrrolidin-2-yl]butan-1-ol 
• 1357981-23-7 (2R,3R,4R)-3,4-bis(benzyloxy)-tetrahydrofuran-2-ol 
• 1357981-14-6 (2R,3S,4S)-4-(benzylamino)-2,3-bis(benzyloxy)-8-(tert-butyldimethylsilyloxy)octan-1-ol 
• 100-39-0 benzyl bromide 
• 130412-79-2 (2R,3R)-2,3-bis(benzyloxy)-4-hydroxybutanoic acid 1,4-lactone 

Downstream Products

• 108866-42-8 (-)-2-epi-lentiginosine 

Relevant academic research and scientific papers

An unexpected high erythro-selection in the Grignard reaction with an N,O-acetal: A concise asymmetric synthesis of indolizidine alkaloid (-)-2-epi-lentiginosine

Starting from commercially available lactone 10, a concise and highly diastereoselective synthesis of (-)-(lS,2R,8aS)-2-epi-lentiginosine (2) is described. The synthesis featured an unexpected highly erythro-selective reaction of Grignard reagent 7 with the protected N,O-acetal 8. The stereochemical outcome of this reaction is contrary to the known results involving the reactions with O-benzyl protected aminofuranosides and aminoglycosides. Thus, this method constitutes an extension of the threo-diastereoselective C-C bond formation methodology.