Stereocontrolled Synthesis of Pseurotin A(2)
| Authors | |
|---|---|
| Year of publication | 2021 |
| Type | Article in Periodical |
| Magazine / Source | Journal of Organic Chemistry |
| MU Faculty or unit | |
| 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. |
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