102152-45-4

Upstream product

• 64312-89-6 Mosher's acid chloride 
• 102152-44-3 tert-butyl 2-ethyl-3-(hydroxymethyl)-4-(1-methyl-5-imidazolyl)-(E)-3-butenoate 
• 102152-36-3 tert-butyl (R)-2-bromobutyrate 
• 102152-42-1 tert-butyl 2-ethyl-3-formyl-4-(1-methyl-5-imidazolyl)-(E)-3-butenoate 
• 102210-88-8 diethylphosphonate 
• 102152-38-5 (E)-tert-butyl 3-cyano-2-ethyl-4-(1-methyl-5-imidazolyl)-3-butenoate 
• 102152-40-9 (Z)-tert-butyl 3-cyano-2-ethyl-4-(1-methyl-5-imidazolyl)-3-butenoate 
• 102152-46-5 tert-butyl 2-ethyl-3-(hydroxymethyl)-4-(1-methyl-5-imidazolyl)-(E)-3-butenoate 
• 102152-37-4 tert-butyl (S)-2-bromobutyrate 
• 102152-43-2 tert-butyl 2-ethyl-3-formyl-4-(1-methyl-5-imidazolyl)-(E)-3-butenoate 
• 102210-88-8 diethylphosphonate 
• 102152-39-6 (E)-tert-butyl 3-cyano-2-ethyl-4-(1-methyl-5-imidazolyl)-3-butenoate 
• 102152-41-0 (Z)-tert-butyl 3-cyano-2-ethyl-4-(1-methyl-5-imidazolyl)-3-butenoate 
• 39637-99-5 (S)-(+)-2-methoxy-2-trifluoromethyl-2-phenylacetyl chloride 

Relevant academic research and scientific papers

Chirospecific Synthesis of (+)-Pilocarpine

An efficient chirospecific synthesis for (+)-pilocarpine (1a) using D-methionine or D-2-aminobutanol as chiral educt is described.Formation of the C3-C4 carbon bond at an early stage gave the key intermediate diethyl phosphonate.Wittig coupling of this phosphonate with 1-methyl-5-imidazolecarboxaldehyde introduced the imidazole moiety of the pilocarpine skeleton.Selective reduction of an α,β-unsaturated nitrile to the corresponding allylic alcohol, stereocontrolled hydrogenation of the olefin, and epimerization of (+)-isopilocarpine to (+)-pilocarpine via kinetic protonation led to formation of the natural alkaloid.This methodology allows chirospecific syntheses of the four possible stereoisomers of pilocarpine.A short and convenient route to (+/-)-pilocarpine based on the key intermediate phosphonate is also described.