Stereocontrolled Synthesis of Pseurotin A(2)

• Autoři: JACHAK Gorakhnath Rajaram; THARRA Prabhakara Rao; SEVELDA Petr; ŠVENDA Jakub
• Rok publikování: 2021
• Druh: Článek v odborném periodiku
• Časopis / Zdroj: Journal of Organic Chemistry
• Fakulta / Pracoviště MU: Přírodovědecká fakulta
• www: https://doi.org/10.1021/acs.joc.1c01152
• Doi: https://doi.org/10.1021/acs.joc.1c01152
• Klíčová slova: Mixtures; Organic compounds; Anions; Solutions; Ethyl groups
• 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.

Související projekty

• CZ-­OPENSCREEN: National Infrastructure for Chemical Biology
• Postdoc@MUNI
• Preklinická progrese nových organických sloučenin s cílenou biologickou aktivitou