1245644-82-9Relevant academic research and scientific papers
Facile Conversion of α-Acyloxy Amides into 3-Hydroxy-lactams
Koszelewski, Dominik,Trzepizur, Damian,Zaorska, Ewelina,Madej, Arleta,Brodzka, Anna,Paprocki, Daniel,Borys, Filip,Wilk, Monika,Ostaszewski, Ryszard
, p. 3280 - 3290 (2018)
The new synthetic route to α-acyloxy amides based on Passerini multicomponent reaction followed by transformation into the corresponding five-, six-, and seven-membered 3-hydroxy-lactams has been proposed. The influence of the reaction conditions, which includes substrate structure on the reaction course that led to desired lactams, was studied. The use of various oxo components in the Passerini multicomponent reaction (P-MCR) has been evaluated. The first example of a semicyclic O,O-acetal employed as an aldehyde equivalent in the P-MCR has been reported. Finally, the established protocol was successfully applied for the enantioselective synthesis of 3-hydroxy-lactams, which play a crucial role in the synthesis of the number of bioactive compounds.
Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid
Romero-Iba?ez, Julio,Cruz-Gregorio, Silvano,Quintero, Leticia,Sartillo-Piscil, Fernando
, p. 2878 - 2886 (2018/07/03)
An asymmetric total synthesis of stereoisomers of a putative structure of 3-hydroxy-2-piperidone alkaloid derivative is described. This route is not only concise and efficient but also is achieved under an environmentally friendly approach. To this end, a direct and double C-H oxidation reaction of simple benzylated piperidine and Baker's yeast reduction of a carbonyl group allowed the rapid access to the optically enriched (S)-1-benzyl-3-hydroxy-2-piperidone in only three steps. The NMR data agreed with those obtained in the first total synthesis (and in discrepancy with the natural product), however, optical rotation did not match with both neither the natural and synthetic material.
