Stereocontrolled Synthesis of Pseurotin A(2)

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Authors	JACHAK Gorakhnath Rajaram THARRA Prabhakara Rao SEVELDA Petr ŠVENDA Jakub
Year of publication	2021
Type	Article in Periodical
Magazine / Source	Journal of Organic Chemistry
MU Faculty or unit	Faculty of Science
Citation
Web	https://doi.org/10.1021/acs.joc.1c01152
Doi	http://dx.doi.org/10.1021/acs.joc.1c01152
Keywords	Mixtures; Organic compounds; Anions; Solutions; Ethyl groups
Description	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.
Related projects:	CZ-OPENSCREEN: National Infrastructure for Chemical Biology Postdoc@MUNI Preclinical Progression of New Organic Compounds with Targeted Biological Activity