Syntheses of doubly linked proanthocyanidins using free flavan units as nucleophiles: insight into the origin of the high regioselectivity of annulation-Reference-Cited by-同舟云学术

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

Published:2019 Issue:41 Volume:17 Page:9129-9134
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Betkekar Vipul V.¹²³⁴,Harachi Mio¹²³⁴,Suzuki Keisuke¹²³⁴^ORCID,Ohmori Ken¹²³⁴^ORCID

Affiliation:

1. Department of Chemistry

2. Tokyo Institute of Technology

3. Meguro-ku

4. Japan

Abstract

Reported herein is a viable synthesis route to procyanidins A1 and A2, doubly linked flavan dimers. The use of nascent nucleophilic partner, catechin or epicatechin, enabled facile regioselective annulation with an ethylenedioxy-bridged flavan unit.

Funder

Japan Society for the Promotion of Science

Nagase Science Technology Foundation

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2019/OB/C9OB01896D

Reference29 articles.

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5. Tannins and related compounds. L Structures of proanthocyanidin A-1 and related compounds.

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