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

Tetrahedron Letters

Volumn 43, Issue 43, 2002, Pages 7659-7662

  Bessières, Bernard ^a   Schoenfelder, Angèle ^a   Verrat, Céline ^a   Mann, André ^a   Ornstein, Paul ^b   Pedregal, Conception ^c  

^a Laboratoire de Pharmacochimie   (France)

^b ELI LILLY AND COMPANY   (United States)

^c ELI LILLY AND COMPANY   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

2 AMINO 4 PHOSPHONOBUTYRIC ACID; ALKENE DERIVATIVE; CARBENOID; CYCLOPROPANE; EGLUMETAD; GLUTAMIC ACID; PHOSPHONIC ACID DERIVATIVE;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; NUCLEAR MAGNETIC RESONANCE; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 0037152266     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)01858-0     Document Type: Article

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27. 31P-decoupled proton spectrum, H-1 appears as a triplet with (J 4.0 Hz), indicating that H-2 and H-3 are trans to H-1 (the cis value would be much larger). In the minor compound H-1 also appears as triplet with a similar coupling constant, therefore the stereochemistry at the cyclopropane ring is the same for the two isomeric compounds 18a/b. The configuration at C-6 has been elucidated through 1D-NOESY. A NOE effect is detected between H-1 and N-H(7) for the major isomer 18a but not for the minor, indicating that H(1) and H(7) are on the same face in the major isomer (18a), and opposite in the corresponding minor one (18b).
28. +: 220.