Toward the total synthesis of ansalactam A

Autor:	Christian A. Kuttruff, Anastasia Hager, Elena Herrero-Gómez, Dirk Trauner
Rok vydání:	2014
Předmět:	Organic Chemistry Total synthesis Context (language use) Biochemistry Radical cyclization Combinatorial chemistry Acylation chemistry.chemical_compound chemistry Reagent Drug Discovery Moiety Xanthate Ansamycins
Zdroj:	Tetrahedron Letters. 55:59-62
ISSN:	0040-4039
DOI:	10.1016/j.tetlet.2013.10.104
Popis:	Ansalactam A is a recently isolated ansa macrolide containing a spiro-γ-lactam functionality that is structurally distinct from other members of the ansa macrolide family. Herein, we describe synthetic studies toward ansalactam A. A route has been developed for the synthesis of a model system featuring a xanthate, which constitutes a direct precursor for the projected radical cyclization step aimed at the formation of the spiro-γ-lactam moiety of ansalactam A. In this context, a new practical method for the removal of an Evans auxiliary attached to sterically encumbered substrates was developed. The utilization of β-lactones as an acylation reagent, an alternative to commonly used amide coupling reactions, is described.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7b5af4fabb710618c3010caa9844f142 https://doi.org/10.1016/j.tetlet.2013.10.104 Zobrazit plný text záznamu Full Text from ScienceDirect