Total syntheses of the squalene-derived halogenated polyethers ent-dioxepandehydrothyrsiferol and armatol A via bromonium- and Lewis acid-initiated epoxide-opening cascades

Autor:	Brian Saxton Underwood, Sze-Sze Ng, Jessica Tanuwidjaja, Timothy F. Jamison
Přispěvatelé:	Massachusetts Institute of Technology. Department of Chemistry, Underwood, Brian Saxton, Tanuwidjaja, Jessica, Ng, SzeSze, Jamison, Timothy F
Jazyk:	angličtina
Rok vydání:	2013
Předmět:	Natural product Organic Chemistry Total synthesis Epoxide Biochemistry Combinatorial chemistry Article Ent-dioxepandehydrothyrsiferol De novo synthesis chemistry.chemical_compound Squalene chemistry Drug Discovery Biogeneses Lewis acids and bases
Zdroj:	PMC
Popis:	Herein we describe in full our investigations leading to the first total syntheses of ent-dioxepandehydrothyrsiferol and armatol A. Discovery of a bromonium-initiated epoxide-opening cascade enabled novel tactics for constructing key fragments found in both natural products and have led us to revise the proposed biogeneses. Other common features found in the routes include convergent fragment coupling strategies to assemble the natural products' backbones and the use of epoxide-opening cascades for rapid constructions of the fused polyether subunits. Through de novo synthesis of armatol A, we elucidate the absolute and relative configuration of this natural product. Elsevier
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::80f10c94479927d9b063540a24e04bd0 https://orcid.org/0000-0002-8601-7799 Zobrazit plný text záznamu