4673-12-5

Upstream product

• 4673-11-4 1-(chloroacetyl)-7-oxo-10-ethyldecahydroquinoline 
• 74170-67-5 2-(1,1-Dioxo-2,5-dihydro-1H-1λ⁶-thiophen-2-yl)-1-(5-ethyl-3,4-dihydro-2H-pyridin-1-yl)-ethanone 
• 74209-58-8 (6aR,9aS,9bS)-6a-Ethyl-5,6,6a,7,9a,9b-hexahydro-1H,4H-pyrrolo[3,2,1-ij]quinolin-2-one 
• 74170-63-1 3-ethyl-3,4,5,6-tetrahydropyridine 
• 73670-94-7 2-(2,5-Dihydro-1,1-dioxothienyl)acetyl chloride 
• 881897-29-6 1-{[benzoyloxy-(2-chloro-allyl)-carbamoyl]-methyl}-3-ethyl-6-oxo-cyclohex-2-enecarboxylic acid methyl ester 
• 1027596-32-2 1-{[(2-chloro-allyl)-hydroxy-carbamoyl]-methyl}-3-ethyl-6-oxo-cyclohex-2-enecarboxylic acid methyl ester 
• 881897-24-1 (+/-)-methyl 5-ethyl-2-methoxy-1-(tert-butoxycarbonylmethyl)cyclohexa-2,5-dienecarboxylate 
• 881897-28-5 methyl 5-ethyl-2,3,3a,6,7,7a-hexahydro-7a-hydroxy-2-oxobenzofuran-3a-carboxylate 
• 112622-41-0 O-(methoxycarbonyl)-N-(chloroacetyl)-N-<(1-methoxy-4-ethylbicyclo<2.2.2>oct-5-en-endo-2-yl)methyl>hydroxylamine 
• 112622-42-1 N-(chloroacetyl)-N-<(1-methoxy-4-ethylbicyclo<2.2.2>oct-5-en-endo-2-yl)methyl>hydroxylamine 
• 112622-51-2 2-Chloro-1-((4aS,8aS)-4a-ethyl-7-methoxy-4a,5,6,8a-tetrahydro-4H-quinolin-1-yl)-ethanone 
• 112622-43-2 1-(chloroacetyl)-7-oxo-10-ethyl-1,4,5,6,7,8,9,10-octahydroquinoline 
• 112622-50-1 (1R,2S,4S)-4-Ethyl-1-methoxy-bicyclo[2.2.2]oct-5-ene-2-carbaldehyde oxime 

Relevant academic research and scientific papers

Amidyls in radical cascades. The total synthesis of (±)-aspidospermidine and (±)-13-deoxyserratine

Concise routes to aspidospermidine and 13-deoxyserratine are described, hinging on a cascade starting from an amidyl radical and allowing the construction of the key indolizidine cores in one step.

A short total synthesis of (±)-aspidospermidine

A cascade radical cyclization starting from an amidyl radical has been used for the construction of (±)-aspidospermidine. This approach has also been developed for the preparation of a tricycle whose framework is contained in the stemona alkaloids.

The 1-Aza-Cope Rearrangement

The 1-aza-Cope rearrangement of azavinylcyclohexene derivatives were investigated.It was observed that an N-acyl substituent on the 1-aza 1,5-diene provides a sufficient driving force for this normally contrathermodynamic process.Although simple derivatives have high activation energies proceeding in relative low overall yield, a methoxy substituent at C-4 of the aza diene as well as its incorporation into strained bicyclic ring systems facilitates the 1-aza-Cope rearrangement.Because the aza diene precursors are readily available by using the Diels-Alder reaction with acrolein derivatives, this process has synthetic potential for the preparation of nitrogen heterocycles.This scheme is illustrated with the preparation of a hydrolulolidine providing a formal total synthesis of (+/-)-aspidospermine.