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A short and efficient synthesis of (S)-4-methylene proline benzyl ester from (S)-pyroglutamic acid

✍ Scribed by Sharad Kumar Panday; Dominique Griffart-Brunet; Nicole Langlois


Book ID
104214683
Publisher
Elsevier Science
Year
1994
Tongue
French
Weight
286 KB
Volume
35
Category
Article
ISSN
0040-4039

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✦ Synopsis


S)-4-merhylene proline benzyl ester 2 was synthesized from benzyl N-terr -butoxycarbonyl pyroglutama~e through a Mannich and a Cope elimination reactions.

Racemic 4-methylene proline is a natural product which has heen isolated from seeds of loquat (Eriobotryajaponicu).l Optically pure Q-1, as structurally modified proline, has been described as potential enzyme inhibitor,293 particularly as inhibitor of proline dehydrogenase. 3 It has also been found to be useful as element of peptides and drugs4 such as tomaymycin analogs.4a


πŸ“œ SIMILAR VOLUMES


ChemInform Abstract: New Amino Acids Der
✍ J. VAN BETSBRUGGE; W. VAN DEN NEST; P. VERHEYDEN; D. TOURWE πŸ“‚ Article πŸ“… 2010 πŸ› John Wiley and Sons βš– 38 KB πŸ‘ 2 views

Pyroglutamic acid derivative (I) is proved to be an excellent chiral starting compound for the synthesis of title amino acids (IX), (X), and (V). The syntheses are based on a combination of methods previously used for the preparation of 4-and 5-substituted prolines. These methods are the ring openin