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This chapter describes the synthetic procedures leading to ether dipeptide isosteres of the Phe-ψ[CH
2
O]-spiro-C
x
(
9a–9e
, Fig. 1 ) and Phe-ψ[CH
2
O]-Allylglycine (
13
, Fig. 2 ). Development of methods which lead to mimetics of amide bonds is central to the conversion of peptide leads into pharmaceutically viable molecules. Our strategy utilizes template
1
, which provides derivatives
6b–6e
upon alkylation with I, Cl-alkanes (C
3
–C
6
). Subsequent Finklestein conversion to iodides
7b–7e
is then followed by cyclization to spirocyclic derivatives
5b–5e
(Fig. 3 ).Figure 1.
Synthesis of Phe ψ[CH
2
O]Spiro isosteres
9a–9e
.
Figure 2.
Synthesis of Phe ψ[CH
2
O]Allylglycine
13
Figure 3.
Synthesis of morpholinones
5b–5e
.
