Concise and Environmentally Friendly Asymmetric Total Synthesis of the Putative Structure of a Biologically Active 3-Hydroxy-2-piperidone Alkaloid

Autor:	Julio Romero-Ibañez, Leticia Quintero, Fernando Sartillo-Piscil, Silvano Cruz-Gregorio
Rok vydání:	2018
Předmět:	Natural product 010405 organic chemistry Alkaloid Organic Chemistry Total synthesis 010402 general chemistry 01 natural sciences Combinatorial chemistry Environmentally friendly Redox Catalysis Yeast 0104 chemical sciences chemistry.chemical_compound chemistry Piperidine Derivative (chemistry)
Zdroj:	Synthesis. 50:2878-2886
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-0037-1610089
Popis:	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.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::a029f64a6d5822edae68db2dec7c12c0 https://doi.org/10.1055/s-0037-1610089 Zobrazit plný text záznamu