A short and efficient synthesis of (S)-4-methylene proline benzyl ester from (S)-pyroglutamic acid
β 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
No coin nor oath required. For personal study only.
β¦ 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
π SIMILAR VOLUMES
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