1427281-93-3

Upstream product

• 1427281-85-3 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1R)-1-phenylethyl]-1,2,3,4-tetrahydropyridine-2-carboxylate 
• 1427281-89-7 (-)-(1R,2S,5R)-8-phenylmenthyl (2S)-4-oxo-1-[(1R)-1-phenylethyl]piperidine-2-carboxylate 
• 178035-47-7 (1S,5R)-2-[(1R)-1-phenylethyl]-6-oxa-2-azabicyclo[3.2.1]octan-7-one 

Relevant academic research and scientific papers

NOVEL PYRROLIDINE COMPOUND AND APPLICATION AS MELANOCORTIN RECEPTOR AGONIST

The present invention relates to a novel pyrrolidine compound having melanocortin receptor agonist activity or a pharmaceutically acceptable salt thereof, and to pharmaceutical applications thereof. The present invention relates to a pyrrolidine derivative represented by formula [I], wherein ring A represents an optionally substituted aryl group or the like; R1 represents an optionally substituted alkyl group or the like; R2 represents a halogen atom or the like; and R3 is an alkyl group substituted with an optionally substituted aryl group or the like, and R4 is a hydrogen atom or the like; or R3 and R4 are terminally attached to each other, and together with the nitrogen atom to which they are attached, form an optionally substituted nitrogen-containing aliphatic heterocyclic ring that may partially contain a double bond; or to a pharmaceutically acceptable salt thereof.

Highly stereoselective cycloadditions of Danishefsky's diene to (-)-8-phenylmenthyl and (+)-8-phenylneomenthyl glyoxylate N-phenylethylimines

Enantiopure 4-oxo-pipecolic acid derivatives were obtained by double asymmetric induction aza-Diels-Alder reactions between chiral glyoxylate N-phenylethylimines and Danishefsky's diene mediated by zinc iodide. The key to success was the use of iminoacetates possessing two chiral auxiliaries, N-(S)- or N-(R)-1-phenylethyl and (-)-8-phenylmenthyl or (+)-8-phenylneomenthyl. Adducts were formed in good yields (78-81%), with complete regioselectivity and high diastereoselectivity (87-96%). The absolute configuration of the adducts formed was unequivocally assigned through NMR, specific optical rotation and X-ray data of appropriated derivatives. These cycloadducts can serve as precursors for bioactive piperidinic azasugars and pipecolic acid derivatives.