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https://hdl.handle.net/2440/76362
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Type: | Journal article |
Title: | Procyanidin oligomers. A new method for 4→8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy |
Other Titles: | Procyanidin oligomers. A new method for 4->8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy |
Author: | Dennis, E. Jeffery, D. Johnston, M. Perkins, M. Smith, P. |
Citation: | Tetrahedron: the international journal for the rapid publication of full original research papers and critical reviews in organic chemistr, 2012; 68(1):340-348 |
Publisher: | Pergamon-Elsevier Science Ltd |
Issue Date: | 2012 |
ISSN: | 0040-4020 1464-5416 |
Statement of Responsibility: | Eric G. Dennis, David W. Jeffery, Martin R. Johnston, Michael V. Perkins, Paul A. Smith |
Abstract: | Interest in the synthesis of procyanidin (catechin or epicatechin) oligomers that contain the 4→8 interflavan linkage remains high, principally due to research into their health effects. A novel coupling utilising a C8-boronic acid as a directing group was developed in the synthesis of natural procyanidin B3 (i.e., 3,4-trans-(+)-catechin-4α→8-(+)- catechin dimer). The key interflavan bond was forged using a novel Lewis acid-promoted coupling of C4-ether 6 with C8-boronic acid 16 to provide the α-linked dimer with high diastereoselectivity. Through the use of a boron protecting group, the new coupling procedure was extended to the synthesis of a protected procyanidin trimer analogous to natural procyanidin C2. © 2011 Elsevier B.V. All rights reserved. |
Keywords: | Iterative synthesis procyanidin oligomers Lewis acid-promoted coupling Benzyl ether procyanidin B3 boron-protection |
Rights: | © 2011 Elsevier Ltd. All rights reserved. |
DOI: | 10.1016/j.tet.2011.10.039 |
Published version: | http://dx.doi.org/10.1016/j.tet.2011.10.039 |
Appears in Collections: | Agriculture, Food and Wine publications Aurora harvest |
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hdl_76362.pdf | Accepted version | 1.35 MB | Adobe PDF | View/Open |
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