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Issue 41, 2019
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Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation

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Abstract

A synthesis method of doubly linked flavan dimers is reported via the acid-promoted annulation reaction using nascent catechins, (+)-catechin or (−)-epicatechin, as a dianionic partner and an ethylenedioxy-bridged flavan as a dicationic partner. Procyanidins A1 and A2 were synthesized. On the high regioselectivity of the annulation reactions, model experiments and computational studies were carried out.

Graphical abstract: Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation

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Publication details

The article was received on 29 Aug 2019, accepted on 27 Sep 2019 and first published on 27 Sep 2019


Article type: Communication
DOI: 10.1039/C9OB01896D
Org. Biomol. Chem., 2019,17, 9129-9134

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    Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation

    V. V. Betkekar, M. Harachi, K. Suzuki and K. Ohmori, Org. Biomol. Chem., 2019, 17, 9129
    DOI: 10.1039/C9OB01896D

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