Epoxyamide-Based Strategy for the Synthesis of Polypropionate-Type Frameworks

Autor:	Francisca Martín-Gálvez, José F. Tejón-Blanco, Samy Chammaa, Miguel Garcia‐Castro, Francisco Sarabia, Antonio Sánchez-Ruiz
Rok vydání:	2008
Předmět:	chemistry.chemical_classification medicine.drug_class Organic Chemistry Diastereomer Epoxide Carboxamide Aldehyde Chemical synthesis chemistry.chemical_compound chemistry Ylide medicine Organic chemistry Stereoselectivity Protecting group
Zdroj:	The Journal of Organic Chemistry. 73:8979-8986
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo801728s
Popis:	A new approach to the stereoselective synthesis of polypropionate-type frameworks is reported utilizing reactions of amide-stabilized sulfur ylides with chiral aldehydes. To establish a new strategy for macrolide fragment synthesis, the stereoselectivity of these reactions in the construction of epoxy amides was the most important aspect of this study. In this aspect, we found a strong influence of the protecting groups employed in the starting aldehydes upon the stereochemical outcome of their reactions with the sulfur ylide 1. Thus, numerous aldehydes showed remarkable stereofacial differentiation, providing a major diastereoisomer, in contrast to others that displayed a poor or no stereoselectivity. Despite the difficulties encountered for some cases with respect to their diastereomeric yields, we were able to prepare various stereotetrads and stereopentads, thus enhancing the synthetic value of this new methodology for the preparation of typical polypropionate frameworks found in many natural products, in particular the macrolide class of antibiotics.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::6c0d22456cc7f413aff7d20c9e383689 https://doi.org/10.1021/jo801728s Zobrazit plný text záznamu