375797-99-2Relevant articles and documents
Transition-Metal-Free Total Synthesis and Revision of the Absolute Configuration of Pipermethystine
Quintero, Leticia,Rodr?guez-Molina, Braulio,Sartillo-Piscil, Fernando,Vázquez-Amaya, Laura Y.
, p. 3949 - 3953 (2020/03/23)
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.