Beilstein J. Org. Chem.2009,5, No. 71, doi:10.3762/bjoc.5.71
molecular framework of the subtype “isoplagiochin” is of substantial structural interest because of the chirality of the entire molecule, which arises from two biaryl axes in combination with two helical two-carbon units in a cyclic arrangement. From a structural as well as a synthetic point of view we
macrocycles.
Keywords: axially chiral biaryl; isoplagiochin; macrocycle; ring strain; total synthesis; Introduction
The cyclic bisbibenzyls isoplagiochin C (1) and D (2) were isolated from the liverworts Plagiochila fruticosa [1], Plagiochila deflexa [2], Herbertus sakuraii [3] and Lepidozia fauriana [4
] (Figure 1). Recently, an increasing number of different biological activities of phenolic compounds of the bisbibenzyl type were reported [5][6][7][8][9][10][11][12].
Furthermore, the isoplagiochin framework proved to be of substantial structural interest because of the chirality of the entire molecule
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Graphical Abstract
Figure 1:
Structures of isoplagiochins C (1) and D (2) (with aryl fragments a–d and possible conformational b...