Synthetic approaches to racemic porantheridine and 8-epihalosaline via a nitroso Diels-Alder cycloaddition/ring-rearrangement metathesis sequence

Autor:	Pierre Sancibrao, Guillaume Vincent, Delphine Karila, Cyrille Kouklovsky
Rok vydání:	2010
Předmět:	Molecular Structure Chemistry Stereochemistry Organic Chemistry Total synthesis Sequence (biology) Stereoisomerism Nitroso Metathesis Ring (chemistry) Chemical synthesis Cycloaddition chemistry.chemical_compound Alkaloids Piperidines Cyclization Piperidine Nitroso Compounds
Zdroj:	The Journal of organic chemistry. 75(12)
ISSN:	1520-6904
Popis:	The application of a sequence involving a nitroso Diels-Alder cycloaddition and a ring-rearrangement metathesis to the total synthesis of (+/-)-8-epihalosaline and the formal synthesis of (+/-)-porantheridine is described. The formation of the 2,6-trans-disubstituted piperidine backbone of porantheridine has been accomplished by addition of a Grignard reagent onto an N-benzylpiperidone followed by a highly diastereoselective reduction of the imminium intermediate in one pot.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::00e109015e13ec0a7bae56c4e353dc26 https://pubmed.ncbi.nlm.nih.gov/20504007 Zobrazit plný text záznamu