Spiroaminal Model Systems of the Marineosins with Final Step Pyrrole Incorporation

Autor:	Cynthia B. Berry, Joseph D. Panarese, Craig W. Lindsley, Leslie N. Aldrich, Leah C. Konkol, Brittney S. Bates
Rok vydání:	2013
Předmět:	Stereochemistry Organic Chemistry Enantioselective synthesis Iminium Ring (chemistry) Biochemistry Medicinal chemistry Article chemistry.chemical_compound Nucleophile chemistry Yield (chemistry) Drug Discovery Lactam Trifluoromethanesulfonate Pyrrole
Zdroj:	Tetrahedron letters. 54(18)
ISSN:	0040-4039
Popis:	In this Letter, we describe a short, six step enantioselective route to spiroaminal lactam model systems reminiscent of marineosins A and B that has been developed starting from either ( R )- or ( S )-hydroxysuccinic acid, respectively, in ∼9% overall yield. This route enables late stage incorporation of the pyrrole ring at C5 via nucleophilic displacement of an iminium triflate salt.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7709900a1acbcc95d305ae41d7a8cd2b https://pubmed.ncbi.nlm.nih.gov/23606772 Zobrazit plný text záznamu Full Text from ScienceDirect