Stereocontrolled Synthesis of Pseurotin A2

Autor:	Jakub Švenda, Petr Sevelda, Prabhakara Rao Tharra, Gorakhnath R. Jachak
Rok vydání:	2021
Předmět:	chemistry.chemical_compound Natural product 010405 organic chemistry Stereochemistry Chemistry Pseurotin A Organic Chemistry Diastereomer 010402 general chemistry 01 natural sciences Chemical synthesis 0104 chemical sciences
Zdroj:	The Journal of Organic Chemistry. 86:11845-11861
ISSN:	1520-6904 0022-3263
DOI:	10.1021/acs.joc.1c01152
Popis:	We report synthesis of two diastereomeric structures previously proposed for the complex secondary metabolite pseurotin A(2). Both structures were accessed from the same building blocks taking advantage of a stereodivergent nickel(II)-iamine-catalyzed 1,4-addition of a chiral 2-alkoxycarbonyl-3(2H)-furanone. Late-stage Csp-Csp(3) cross-coupling of a highly functionalized bromoalkyne featured in the pseurotin A(2) side-chain assembly. The work supports the 2016 stereochemical revision of pseurotin A(2) and represents the first chemical synthesis of this natural product.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::7cf971a7994f914690f63f7b048ba4c2 https://doi.org/10.1021/acs.joc.1c01152 Zobrazit plný text záznamu