Short Synthesis of (+)-Actinobolin: Simple Entry to Complex Small-Molecule Inhibitors of Protein Synthesis

Autor:	Prabhakara R. Tharra, Andrey A. Mikhaylov, Jiří Švejkar, Marina Gysin, Sven N. Hobbie, Jakub Švenda
Přispěvatelé:	University of Zurich, Švenda, Jakub
Rok vydání:	2021
Předmět:	Molecular Structure 10179 Institute of Medical Microbiology 1503 Catalysis 570 Life sciences biology 610 Medicine & health 1600 General Chemistry Stereoisomerism General Medicine General Chemistry Catalysis Pyrans
Zdroj:	Angewandte Chemie (International ed. in English). 61(17)
ISSN:	1521-3773
Popis:	We report a concise synthesis of the naturally occurring protein synthesis inhibitor (+)-actinobolin (1). The densely functionalized and stereochemically complex molecular structure of 1 was assembled from (-)-quinic acid, L-threonine, and L-alanine as the principal components. Our route is based around a convergent strategy that features conjugate addition of an α-amino radical in the key fragment-coupling step. The dramatically simplified synthesis of (+)-actinobolin proceeding in 9 steps with 18 % overall yield has practical implications for analog preparation, as demonstrated herein.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::21dece570054e402b57c9bc1f287025f https://pubmed.ncbi.nlm.nih.gov/35167723 Zobrazit plný text záznamu Plný text