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Asymmetric Synthesis of Bioactive Lactones and the Development of a Catalytic Asymmetric Synthesis of α-Aryl Ketones pp 35–56Cite as

Asymmetric Synthesis of Both Enantiomers of a δ-Lactone Analogue of Muricatacin

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Abstract

The asymmetric synthesis of both enantiomers of the δ-lactone analogue of the anti-tumoral natural product γ-lactone muricatacin has been carried out in a 9-step sequence with overall yields of 17.8 and 11.2 %, respectively. Initial attempts to also synthesise the natural product proved unsuccessful due to the poor reactivity of the Grignard reagent derived from 2-(bromomethyl)-1,3-dioxolane. The designed synthetic route enabled us to increase the ring size to generate the δ-lactone analogue employing Sharpless asymmetric epoxidation and ZrCl4-catalysed intramolecular acetalisation as the key steps.

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  1. Department of Chemistry, Imperial College London, London, UK

    Robert Doran

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  1. Robert Doran
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Doran, R. (2015). Asymmetric Synthesis of Both Enantiomers of a δ-Lactone Analogue of Muricatacin. In: Asymmetric Synthesis of Bioactive Lactones and the Development of a Catalytic Asymmetric Synthesis of α-Aryl Ketones. Springer Theses. Springer, Cham. https://doi.org/10.1007/978-3-319-20544-1_3

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