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Review
. 2007 Aug 29;12(9):2106-22.
doi: 10.3390/12082106.

Bile acid scaffolds in supramolecular chemistry: the interplay of design and synthesis

Anthony P Davis  1
Affiliations
Review

Bile acid scaffolds in supramolecular chemistry: the interplay of design and synthesis

Anthony P Davis. Molecules. .

Abstract

Since early work in the 1980s, the bile acids have become well established as building blocks for supramolecular chemistry. The author's laboratory has specialised in converting cholic acid, the archetypal bile acid, into macrocyclic and acyclic receptors for anions and carbohydrates. This review highlights the synthetic aspects of this work, especially the use of modern synthetic methodology to perform less obvious structural transformations.

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Figures

Figure 1
Figure 1
Cholic acid 1 with numbering system (blue).
Scheme 1
Scheme 1
Scheme 2
Scheme 2
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Scheme 3
Scheme 4
Scheme 4
Figure 2
Figure 2
Scheme 5
Scheme 5
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Scheme 6
Scheme 7
Scheme 7
Figure 3
Figure 3
Restricted rotation about axial C-N bonds in cholapod receptors.
Scheme 8
Scheme 8
See this image and copyright information in PMC

References

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    1. We estimate that at least 40 groups have contributed to the area.

    1. Davis A. P., Wareham R. S. Carbohydrate recognition through noncovalent interactions: A challenge for biomimetic and supramolecular chemistry. Angew. Chem., Int. Ed. 1999;38:2978–2996. doi: 10.1002/(SICI)1521-3773(19991018)38:20<2978::AID-ANIE2978>3.0.CO;2-P. - DOI - PubMed

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