Facile synthesis of (−)-6-acetoxy-5-hexadecanolide by size-selective ring-closing/cross metathesis

Autor:	Kevin J. Quinn, Neal A. Biddick, Kevin P. McGrath, John M. Curto
Rok vydání:	2009
Předmět:	chemistry.chemical_classification Stereochemistry Organic Chemistry Total synthesis Ring (chemistry) Metathesis Biochemistry chemistry Yield (chemistry) Drug Discovery Salt metathesis reaction Ring-opening metathesis polymerisation Alkyl Acyclic diene metathesis
Zdroj:	Tetrahedron Letters. 50:7121-7123
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2009.09.179
Popis:	A total synthesis of (−)-6-acetoxy-5-hexadecanolide, in six steps and 37% overall yield from (2 R ,3 S )-1,2-epoxy-4-penten-3-ol is reported. The key synthetic step is a size-selective ring-closing/cross metathesis reaction in which lactone formation and alkyl chain extension are accomplished in an efficient one-pot process.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::53aefec6dbdcf7be1dc4603da4c58fe1 https://doi.org/10.1016/j.tetlet.2009.09.179 Zobrazit plný text záznamu Full Text from ScienceDirect