The synthesis of sterically demanding amino acid-derived cyclic phosphonamides.
The preparation and utilization of C(2)-symmetric 1,4-diamines in the synthesis of amino acid-derived cyclic phosphonamides 1-3 are described. The 1,4-diamines are synthesized via three methods: (i) amino acid/fumaryl chloride coupling followed by amide reduction, (ii) amino acid/1,4-diamine coupling followed by amide reduction, and (iii) a template-supported ring-closing metathesis/hydrolysis sequence. The pseudo C(2)-symmetric cyclic phosphonamides 1-3 are prepared by condensation of the C(2)-symmetric 1,4-diamines to P(III) centers, followed by oxidation.
Sprott
K T
KT
Department of Chemistry, Malott Hall, University of Kansas, Lawrence, Kansas 66045, USA.
Hanson
P R
PR
D017320:HIV Protease Inhibitors / Q000138:chemical synthesis*
D017320:HIV Protease Inhibitors