The Development of Novel Antibiotics Using ... - Jacobs University

Scope of Work
enhance their recognition ability, it was necessary to synthesize selectively the C 3 -symmetrical
trianglimines. All attempts to synthesize C 3 -symmetrical biphenyl dialdehydes of the type 4
(Figure 3.2) did not succeed.
Figure 3.1 Molecular recognition of Vancomycin to D-Ala-D-Ala.
The basic structure of trianglimine macrocycles (i.e., 7) contains many attractive features such as
the conformational bias of the (1R,2R)-1,2-diaminocyclohexane ring, the ability to introduce
functionalities into the aromatic moieties, the chirality and most importantly the dynamic
reversibility of the imine covalent bonds (Figure 3.3). An interesting idea, which came to mind
was replacing the (1R,2R)-1,2-diaminocyclohexane units by dicarbohydrazides (i.e., 8), which
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