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Synthesis of constrained cycloalkyl analogues of glutamic acid with an ω-phosphonic acid function

✍ Scribed by Bernard Bessières; Angèle Schoenfelder; Céline Verrat; André Mann; Paul Ornstein; Conception Pedregal

Publisher
Elsevier Science
Year
2002
Tongue
French
Weight
132 KB
Volume
43
Category
Article
ISSN
0040-4039

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✦ Synopsis

A general method based on the sequential reactivities of bis-bromocycloalkenes (3-5) is proposed for the preparation of phosphonocycloalkanes (1a/b-3a/b), representing structural constrained analogues of AP4. For the synthesis of an additional congested AP4 analogue (4), an intramolecular cyclopropanation of a ketocarbene towards a vinyphoshonate, assisted by Rh(OAc) 2 was successfully experimented.

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Synthesis and Proteinase Inhibitory Properties of Diphenyl Phosphonate Analogues of Aspartic and Glutamic Acids. -The title compounds (X) function as irreversible inactivators of S. aureus V8 protease. (Xb) is 10-fold more active than (Xa). -(HAMILTON, R.; WALKER, B.;