Atroposelective Total Synthesis of Darobactin A

Autor:	You-Chen Lin, Fabian Schneider, Kelly J. Eberle, Debora Chiodi, Hugh Nakamura, Solomon H. Reisberg, Jason Chen, Masato Saito, Phil S. Baran
Rok vydání:	2022
Předmět:	Colloid and Surface Chemistry Phenylpropionates Cyclization Alkynes General Chemistry Amino Acids Biochemistry Catalysis
Zdroj:	Journal of the American Chemical Society. 144:14458-14462
ISSN:	1520-5126 0002-7863
Popis:	A concise, modular synthesis of the novel antibiotic darobactin A is disclosed. The synthesis successfully forges the hallmark strained macrocyclic ring systems in a sequential fashion. Key transformations include two atroposelective Larock-based macrocyclizations, one of which proceeds with exquisite regioselectivity despite bearing an unprotected alkyne. The synthesis is designed with medicinal chemistry considerations in mind, appending key portions of the molecule at a late stage. Requisite unnatural amino acid building blocks are easily prepared in an enantiopure form using C-H activation and decarboxylative cross-coupling tactics.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::4ea7939a6f7c5118e6f9934070ad2040 https://doi.org/10.1021/jacs.2c05892 Zobrazit plný text záznamu