375797-99-2

Usage

Occurrence

A piperidine alkaloid, this base occurs in the ethanolic extract of Piper methysticum.

Upstream product

• 645-45-4 hydrocinnamic acid chloride 
• 375366-19-1 (+/-)-4,5-epoxy-N-(1-oxo-3-phenylpropyl)-3,4,5,6-tetrahydro-2(1H)-pyridone 
• 375366-18-0 3,6-dihydro-N-(1-oxo-3-phenylpropyl)-2(1H)-pyridone 
• 61892-77-1 1,6-dihydropyridin-2(3H)-one 
• 72717-68-1 N-allyl-3-butenamide 
• 108-05-4 vinyl acetate 
• 375366-20-4 (+/-)-5,6-dihydro-5-hydroxy-N-(1-oxo-3-phenylpropyl)-2(1H)-pyridone 
• 108-24-7 acetic anhydride 
• 375366-22-6 (R)-5,6-dihydro-5-hydroxy-N-(1-oxo-3-phenylpropyl)-2(1H)-pyridone 

Relevant academic research and scientific papers

Transition-Metal-Free Total Synthesis and Revision of the Absolute Configuration of Pipermethystine

Starting from 3-hydroxy piperidines, a novel transition-metal-free strategy to 5-hydroxy-5,6-dihydro-2(1H)pyridones is reported. This unprecedented approach, which provides a practical, economical, and ecofriendly alternative to either the classical ring-closing metathesis of N-homoallyl-unsaturated amides or the dehydrogenation of amides, occurs by means of a triple C-H functionalization of three unreactive piperidine sp3 carbons. The completion of the total synthesis revealed that the natural levo-isomer possesses the R absolute configuration, not S.

Facile enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones. First total synthesis of both enantiomers of pipermethystine.

[reaction: see text]. A novel enantiodivergent approach to 5-hydroxy-5,6-dihydro-2(1H)-pyridones using a ring closing metathesis and a lipase-mediated kinetic resolution as key steps is described and applied to the first synthesis of both enantiomers of pipermethystine.