59556-15-9

Upstream product

• 72431-21-1 ethyl 1,4-cyclohexadiene-1-carboxylate 
• 3315-16-0 silver cyanate 
• 75-65-0 tert-butyl alcohol 
• 24424-99-5 di-tert-butyl dicarbonate 
• 105897-67-4 C₂₀H₂₁N₃O₃S₂ 
• 89622-09-3 (1S,2R,3R,5S)-2,3-Dibromo-5-tert-butoxycarbonylamino-cyclohexanecarboxylic acid methyl ester 
• 89622-08-2 (1R,5R)-5-tert-Butoxycarbonylamino-cyclohex-2-enecarboxylic acid methyl ester 
• 89622-07-1 7-azabicyclo[3.2.1]oct-3-en-6-one 
• 4103-88-2 1-isocyano-3-cyclohexene 
• 4771-80-6 1,2,5,6-tetrahydrobenzoic acid 
• 105917-29-1 1-(tert-Butyl-dimethyl-silanyl)-5-ethoxy-3-phenylsulfanyl-3-(5-trimethylsilanyl-pent-3-ynyl)-pyrrolidin-2-one 
• 108634-71-5 6-(tert-butoxycarbonyl)-1-(phenylthio)-6-azabicyclo<3.2.1>-3-octen-7-one 
• 105897-65-2 1-(phenylthio)-4-vinylidene-6-azabicyclo<3.2.1>octan-7-one 
• 105897-66-3 1-(phenylthio)-6-azabicyclo<3.2.1>octane-4,7-dione 

Downstream Products

• 59556-18-2 5-amino-1,3-cyclohexadiene-1-carboxylic acid 
• 59556-17-1 gabaculin 

Relevant academic research and scientific papers

REGIOSELECTIVE SYNTHESIS OF (+/-)-GABACULINE

(+/-)-Gabaculine has been synthesized via an intramolecular reaction of an N-acyliminium intermediate with a propargyl silane, followed by allene ozonolysis and a Shapiro reaction.

A novel synthetic route to 6-azabicyclooct-3-enes via silicon directed N-acyliminium chemistry. Synthesis of (+/-)-gabaculine

Alkylation of the lithium enolate, derived from 5-ethoxy-2-pyrrolidone 1 (Scheme 1), using alkyl halides containing either the vinylsilane or 2-propynylsilane moiety, provides substrates 3 for cyclization studies passing through N-acyliminium intermediate

REGIOSELECTIVE SYNTHESIS OF (+/-)-GABACULINE HYDROCHLORIDE

3-Cyclohexenecarboxylic acid (2) has been functionalized to the protected amino acid 5 in a novel reaction sequence, the crucial step being the acid catalysed cyclization of the γ,δ-unsaturated isocyanate 3 to the bicyclic lactam 4. 5 was converted into gabaculine hydrochloride (l HCl).