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Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

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Abstract

Enantioselective syntheses of decytospolide A and decytospolide B are described here. The current synthesis highlights an Achmatowicz rearrangement of an optically active furanyl alcohol followed by reduction of the resulting dihydropyranone hemiacetal with BF3·OEt2 and Et3SiH to provide the saturated tetrahydropyranyl alcohol directly. This reduction was investigated with a variety of other Lewis acids. The synthesis also features Noyori asymmetric transfer hydrogenation and Friedel–Crafts acylation. Overall, the synthesis provides ready access to the natural products and may be useful in the preparation of bioactive derivatives.

Graphical abstract: Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

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Publication details

The article was received on 28 Jun 2018, accepted on 30 Jul 2018 and first published on 07 Aug 2018


Article type: Paper
DOI: 10.1039/C8OB01529E
Citation: Org. Biomol. Chem., 2018, Advance Article
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    Enantioselective total synthesis of decytospolide A and decytospolide B using an Achmatowicz reaction

    A. K. Ghosh, H. M. Simpson and A. M. Veitschegger, Org. Biomol. Chem., 2018, Advance Article , DOI: 10.1039/C8OB01529E

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