132015-11-3

Upstream product

• 89366-20-1 methyl glyoxylate N-tosylhydrazone 
• 1165952-91-9 cyclohexa-1,3-diene 

Downstream Products

• 131895-69-7 (1R,4R,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decane-6,9-diol 
• 131895-69-7 (1R,4S,6R,8R,9R)-4-Methyl-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decane-6,9-diol 
• 131927-16-7 (1R,4S,5S,7R,8R)-8-Hydroxy-6-(toluene-4-sulfonyl)-4-(toluene-4-sulfonyloxy)-6-aza-bicyclo[3.2.1]octane-7-carboxylic acid methyl ester 
• 131895-68-6 (1R,6R,8R,9R)-4-Methyl-9-(tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decan-6-ol 
• 131895-67-5 (1R,5R,7R,8R)-3-Oxo-8-(tetrahydro-pyran-2-yloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]octane-7-carbaldehyde 
• 131895-65-3 (1R,6R,8R,9R)-9-(Tetrahydro-pyran-2-yloxy)-2-(toluene-4-sulfonyl)-5-oxa-2-aza-tricyclo[4.3.1.0^3,8]decan-4-ol 
• 131895-66-4 [(1R,5R,7R,8R)-8-(Tetrahydro-pyran-2-yloxy)-6-(toluene-4-sulfonyl)-6-aza-bicyclo[3.2.1]oct-3-en-7-yl]-methanol 
• 131895-70-0 N-tosylactinobolamine methyl acetal 
• 131895-63-1 (1S,2S,4R,5S,7S)-6-(Toluene-4-sulfonyl)-3-oxa-6-aza-tricyclo[3.2.2.0^2,4]nonane-7-carboxylic acid methyl ester 

Relevant academic research and scientific papers

Participation of Sulphonamide Nitrogen in the Rearrangement of the 2-Azabicyclooctane Skeleton: an Efficient Synthesis of the 6-Azabicyclooctan-4-one System

Treatment of the 2-azabicyclooct-5-ene imino Diels-Alder adduct (2) with N-bromosuccinimide in aqueous dimethoxyethane gives the rearranged bromohydrin (4a), whose structure is confirmed by X-ray crystallographic analysis, and which serves as a precursor to the 6-azabicyclooctan-4-one (7).

A Stereoselective Synthesis of (+/-)-Actinobolamine

A three-step sequence involving an imino ester heterocycloaddition, stereoselective epoxidation of the adduct 4 and subsequent toluene-p-sulphonic acid-promoted rearrangement afforded the 6-azabicyclooctane 7 in excellent overall yield; elaboration