A General Strategy for the Synthesis of Truxinate Natural Products Enabled by Enantioselective [2+2] Photocycloadditions

A General Strategy for the Synthesis of Truxinate Natural Products Enabled by Enantioselective [2+2] Photocycloadditions

Pseudodimeric cyclobutanes constitute a large class of natural products that could, in principle, be efficiently synthesized via [2+2] photocycloadditions. However, the difficulty in developing chemo-, regio-, diastereo-, and enantioselective cycloadditions has limited their use in asymmetric synthe...

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Veröffentlicht in:Journal of the American Chemical Society 2023-09, Vol.145 (35), p.19182-19188
Hauptverfasser: Genzink, Matthew J., Rossler, Matthew D., Recendiz, Herman, Yoon, Tehshik P.
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container_issue 35
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container_title Journal of the American Chemical Society
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creator Genzink, Matthew J.
Rossler, Matthew D.
Recendiz, Herman
Yoon, Tehshik P.
description Pseudodimeric cyclobutanes constitute a large class of natural products that could, in principle, be efficiently synthesized via [2+2] photocycloadditions. However, the difficulty in developing chemo-, regio-, diastereo-, and enantioselective cycloadditions has limited their use in asymmetric syntheses. Herein, we show that chiral acid catalysts promote highly selective visible-light photocycloadditions, the products of which can be quickly transformed into truxinate natural products. This general approach has enabled the synthesis of both dimeric and pseudodimeric cyclobutane natural products with excellent enantioselectivity.
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title A General Strategy for the Synthesis of Truxinate Natural Products Enabled by Enantioselective [2+2] Photocycloadditions
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