O

Template "Type II"

Scheme 3.2.2. (i) Coupling of template type I and linker-head intermediate. (ii) Deprotection, leading to compounds such as 8. (iii) Coupling of template type II and head group. (iv) Deprotection, leading to compounds such as 9.

Scheme 3.2.7 shows the formation of dicarboxy template 2, starting by double alkylation of 1 with methyl bromoacetate and sodium hydride, followed by saponification. Target compound 18 was achieved by amide coupling of 2 with intermediate 16 in the presence of EDC and again cleavage of the Boc groups.

To create target inhibitors with more flexible side chains and reduced molecular weights we attached protected aminopentane tethers to both hydroxy groups of scaffold 1, via double substitution reaction, leading to the formation of ether

AcO AcO

AcO AcO

Ref. 27

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