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

Robert Doran; Patrick J. Guiry

doi:10.1055/s-0033-1340850

Synthesis, Table of Contents

Synthesis 2014; 46(06): 761-770
DOI: 10.1055/s-0033-1340850

paper

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

Robert Doran

Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland Fax: +353(1)7162501 Email: patrick.guiry@ucd.ie

,

Patrick J. Guiry*

Centre for Synthesis and Chemical Biology, School of Chemistry and Chemical Biology, University College Dublin, Belfield, Dublin 4, Ireland Fax: +353(1)7162501 Email: patrick.guiry@ucd.ie

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Abstract

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Abstract

The asymmetric synthesis of both enantiomers of the δ-lactone analogue of the antitumoral natural product γ-lactone muricatacin has been carried out. Initial attempts to also synthesize 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-catalyzed intramolecular acetalization as the key steps.

Key words

muricatacin - asymmetric synthesis - zirconium tetrachloride - natural product analogues - δ-lactone

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References

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