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

ABSTRACT: 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.

SUBMITTER: Genzink MJ

PROVIDER: S-EPMC10528511 | biostudies-literature | 2023 Sep

REPOSITORIES: biostudies-literature

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

Genzink Matthew J MJ Rossler Matthew D MD Recendiz Herman H Yoon Tehshik P TP

Journal of the American Chemical Society 20230821 35

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 gener ...[more]

PMID: 37603410

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