Issue 41, 2019

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

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

Supplementary files

Article information

Article type
Communication
Submitted
29 ago 2019
Accepted
27 set 2019
First published
27 set 2019

Org. Biomol. Chem., 2019,17, 9129-9134

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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