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Issue 46, 2016
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Stereoselective construction of 2-vinyl 3-hydroxybenzopyran rings: total syntheses of teadenols A and B

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Abstract

Total syntheses of teadenols A and B, isolated from fermented tea, were accomplished in a highly stereocontrolled manner. Key steps were an organocatalytic asymmetric α-aminoxylation reaction of an aldehyde and a palladium-catalyzed intramolecular allylic substitution with phenol. In the latter reaction, we utilized the different conformational preferences of cyclic and acyclic carbonate precursors to obtain cis- and trans-fused benzopyran rings, respectively, via intramolecular etherification.

Graphical abstract: Stereoselective construction of 2-vinyl 3-hydroxybenzopyran rings: total syntheses of teadenols A and B

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Publication details

The article was received on 12 Sep 2016, accepted on 19 Oct 2016 and first published on 19 Oct 2016


Article type: Communication
DOI: 10.1039/C6OB02004F
Citation: Org. Biomol. Chem., 2016,14, 10783-10786
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    Stereoselective construction of 2-vinyl 3-hydroxybenzopyran rings: total syntheses of teadenols A and B

    R. Yoshida, H. Ouchi, A. Yoshida, T. Asakawa, M. Inai, M. Egi, Y. Hamashima and T. Kan, Org. Biomol. Chem., 2016, 14, 10783
    DOI: 10.1039/C6OB02004F

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