Martin Kranz, H. Kessler
Jul 22, 1996
Citations
0
Influential Citations
7
Citations
Journal
Tetrahedron Letters
Abstract
Abstract A new strategy for the synthesis of Boc-Phe ψ ( E -CHCH)GlyOH ( 11 ) is described. The double bond is generated employing a β elimination of the mesyloxy group of 6 . This elimination proves to be the key step within the synthesis. Different products are obtained dependent on the base as well as on the reaction conditions. Employing KO t Bu leads to E -(5 S )-( t -Butyloxycarbonylamino)-6-phenyl-1,3-hexadiene 7 whereas NaOMe causes a γ elimination resulting the aziridine 9 . Diene 7 is converted into the corresponding Phe ψ ( E -CHCH)Gly isostere by subsequent hydroboration and Jones oxidation.