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Synthesis 2014; 46(06): 761-770
DOI: 10.1055/s-0033-1340850
DOI: 10.1055/s-0033-1340850
paper
Asymmetric Synthesis of Both Enantiomers of a δ-Lactone Analogue of Muricatacin
Further Information
Publication History
Received: 18 December 2013
Accepted after revision: 03 February 2014
Publication Date:
21 February 2014 (online)
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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-lactoneSupporting Information
- for this article is available online at http://www.thieme-connect.com/ejournals/toc/synthesis.
- Supporting Information
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