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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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Article information


Submitted
29 Aug 2019
Accepted
27 Sep 2019
First published
27 Sep 2019

Org. Biomol. Chem., 2019,17, 9129-9134
Article type
Communication

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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