Synthesis of cylindricine C and a formal synthesis of cylindricine A

Autor:	Gráinne C. Hargaden, Timothy J. Donohoe, Ptoton M. Brian, Timothy J. C. O'Riordan
Rok vydání:	2016
Předmět:	chemistry.chemical_classification Natural product Pyridinium Compounds Stereochemistry Organic Chemistry Regioselectivity Cylindricine Biochemistry Chemical synthesis chemistry.chemical_compound Formal synthesis chemistry Drug Discovery heterocyclic compounds Pyridinium Alkyl
DOI:	10.1016/j.tet.2010.05.044
Popis:	This paper reports the synthesis of the alkaloid natural product (±)-cylindricine C, in addition to a formal synthesis of (±)-cylindricine A. The key step in our sequence is the (ipso) regioselective addition of an alkyl Grignard reagent to a C-2 substituted pyridinium salt to generate the dihydropyridone core of the alkaloid targets. After cyclisation to form the A and C rings of the cyclindricines the net outcome is a short (13 steps) synthesis of this natural product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::65ebcdaf56f16b2cc439c55494318733 https://doi.org/10.1016/j.tet.2010.05.044 Zobrazit plný text záznamu