886038-16-0

Upstream product

• 52890-22-9 ethyl 3-(2-methylidenecyclohexyl)propionate 
• 6638-79-5 N,O-dimethylhydroxylamine*hydrochloride 
• 1125-99-1 1-(1-Cyclohexen-1-yl)pyrrolidine 
• 97022-10-1 3-(2-Pyrrolidin-1-yl-cyclohex-1-enyl)-propionic acid ethyl ester 
• 4095-02-7 3-(2-oxocyclohexyl)propionic acid ethyl ester 
• 108-94-1 cyclohexanone 

Downstream Products

• 886038-15-9 1-(2-methylidenecyclohexyl)-nonan-3-one 
• 1258206-79-9 1-(2-methylenecyclohexyl)heptan-3-one 

Relevant academic research and scientific papers

Efficient carboazidation of alkenes using a radical desulfonylative azide transfer process

The radical-mediated carboazidation of terminal alkenes using electrophilic alkanesulfonyl azides is reported. A single reagent delivers the necessary electrophilic alkyl radical as well as the azido group, and good yields are obtained by using a moderate excess of the carboazidating reagent (1.5-2 equiv). Interestingly, in addition to the starting sulfonyl azide, this method requires only the use of a radical initiator, di-tert-butyldiazene. In terms of atom economy, this azide transfer reaction is close to ideal, as SO2 (1 equiv) is the only side product. The synthetic potential of this process has been demonstrated by a formal synthesis of the alkaloid lepadiformine C.

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.