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

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can be obtained from commercially available tartaric acid in both enantiomeric forms (R or S).
Dihydrazides (i.e., 8) possess high reactivity in comparison with trans-(1R,2R)-diaminocyclohexane
3. It is worth noting that the macrocycles obtained by reacting the protected dicarbohydrazides
with aromatic dialdehydes in [2+2]-cyclocondensation reactions have not been
previously reported in literature and constitute a novel class of structurally unique architectures
with intriguing design. 7,8
The novel macrocycles obtained by this approach were named tetra-carbohydrazide cyclophanes.
A comparison between trianglimine structure and the structure of the novel cyclophane
macrocycles is shown in Figure 3.4. In addition to all attractive features present in trianglimine
structure, tetra-carbohydrazide cyclophanes possess four carbonyl moieties, which can function
as extra binding motifs (Figure 3.4). Tetra-carbohydrazide cyclophanes underwent successfully
dynamic exchange in a mixture of DMF/MeOH and in presence of catalytic AcOH to form a
DCL of macrocycles possessing mixed building blocks with different structures of the type
shown in Figure 3.5. 9
Figure 3.2 C 3 -symmetrical 5 and non-symmetrical 6 trianglimines obtained from 2.
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