Procyanidin oligomers. A new method for 4->8 interflavan bond formation using C8-boronic acids and iterative oligomer synthesis through a boron-protection strategy

Eric Dennis, David Jeffery, Martin Johnston, Michael Perkins, Paul Smith

    Research output: Contribution to journalArticle

    10 Citations (Scopus)

    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.

    Original languageEnglish
    Pages (from-to)340-348
    Number of pages9
    JournalTetrahedron
    Volume68
    Issue number1
    DOIs
    Publication statusPublished - 2012

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