The syntheses of rac-inthomycin A, (+)-inthomycin B and (+)-inthomycin C using a unified synthetic approach

Autor:	Michael R. Webb, Xavier Franci, Mathieu Pizzonero, Richard J. K. Taylor, Craig S. Donald, James Dale, Matthew S. Addie, Catherine M. Crawforth
Rok vydání:	2008
Předmět:	biology Stereochemistry Organic Chemistry Acetal Ketene biology.organism_classification Biochemistry Streptomyces Stereocenter Stille reaction chemistry.chemical_compound chemistry Inthomycin C Aldol reaction Drug Discovery Oxazole
Zdroj:	Tetrahedron. 64:4778-4791
ISSN:	0040-4020
DOI:	10.1016/j.tet.2008.01.116
Popis:	The Stille coupling between a common oxazole vinyl iodide and stereodefined stannyl-diene units is described as the cornerstone of a unified synthetic route to the inthomycin family of bioactive Streptomyces metabolites. This procedure has been utilised to prepare (+)-inthomycin B and (+)-inthomycin C for the first time; in these examples the stereogenic centre was introduced using the Kiyooka ketene acetal/amino acid-derived oxazaborolidinone variant of the Mukaiyama aldol reaction. In addition, a convenient preparation of rac-inthomycin A is described based on the same strategy.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::90c80ddc646b91eed52e9f6a0400deaf https://doi.org/10.1016/j.tet.2008.01.116 Zobrazit plný text záznamu Full Text from ScienceDirect