97022-10-1

Upstream product

• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 140-88-5 ethyl acrylate 
• 108-94-1 cyclohexanone 

Downstream Products

• 31887-89-5 1-benzyl-3,4,5,6,7,8-hexahydro-2(1H)-quinolinone 
• 4095-02-7 3-(2-oxocyclohexyl)propionic acid ethyl ester 
• 886038-15-9 1-(2-methylidenecyclohexyl)-nonan-3-one 
• 52890-22-9 ethyl 3-(2-methylidenecyclohexyl)propionate 
• 886038-16-0 3-(2-methylidenecyclohexyl)-N-methoxy-N-methylpropanamide 

Relevant academic research and scientific papers

Total synthesis of the marine alkaloid (±)-lepadiformine via a radical carboazidation

The total synthesis of lepadiformine has been achieved in 10 steps and 15% overall yield from cyclohexanone. The amino-substituted quaternary carbon center is created through a radical carboazidation reaction. The tricyclic core of lepadiformine is built via an efficient hydrogenation process, involving reduction of the azide and intramolecular reductive amination of a ketone, followed by lactamization of the intermediate γ-aminoester. The hydroxymethyl side chain is introduced according to a modified Takahata procedure after conversion of the lactam into a thiolactam.

ENAMINE CHEMISTRY-XVIII. THE FORMATION OF HEXAHYDROCHROMANE-8a-AMINES BY REDUCTIVE CYCLISATION OF ENAMINES

Enamines (1) derived from cyclohexanone or cyclopentanone are reacted with electrophilic olefins (ethyl acrylate, ethyl 2-methylacrylate, ethyl 2-butenoate) to give the new enamines, 2.When 2 is reacted with LiAlH4, reductive cyclisation takes place giving hexahydrochromane-8a-amines of octahydrocyclopentapyrane-7a-amines, 3, in quantitative yields, 3 is hydrolyzed with dilute aqueous hydrochloric acid to hexahydrochromane-8a-ols of octahydrocyclopentapyrane-7a-ols (4) and reacts also with oxalic acid in refluxing dioxane to form the condensed dihydropyranes, 5.