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

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

• References

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