134107-63-4Relevant academic research and scientific papers
Functionalised pyrrolidinones derived from (S)-pyroglutamic acid
Beard, Mark J.,Bailey, Jonathan H.,Cherry, David T.,Moloney, Mark G.,Shim, Sung Bo,Statham, Kathryn A.,Bamford, Mark J.,Lamont, R. Brian
, p. 3719 - 3740 (2007/10/03)
The generation of the lactam enolate derived from bicyclic lactams 2a-c, prepared from (S)-pyroglutamic acid 1a, and subsequent reaction with a range of electrophiles, is reported. Exo-diastereoselectivity is generally favoured. The deprotection of some of these adducts to give functionalised hydroxymethylpyrrolidinones is readily achieved by simple hemiaminal ether cleavage under acidic conditions.
Efficient total synthesis of AI-77-B, a gastroprotective substance from Bacillus pumilus AI-77
Hamada,Hara,Kawai,Kohno,Shioiri
, p. 8635 - 8652 (2007/10/02)
First total synthesis of AI-77-B (1), a gastroprotective substance from Bacillus pumilus AI-77, was achieved in a stereoselective and convergent manner. In this synthesis, the dihydroisocoumarin part 2 was constructed in one step through 1,2-addition of the benzylic anion 17b to Boc-L-leucinal 7b. The hydroxy amino acid 4 was elaborated from (R)-glutamic acid in a highly stereoselective manner. Condensation of 2·HCl and 4, intramolecular Pinner reaction, followed by mild hydrolysis afforded AI-77-B (1).
(L)-pyroglutamic acid as a chiral starting material for asymmetric synthesis
Baldwin, Jack E.,Moloney, Mark G.,Shim, Sung Bo
, p. 1379 - 1380 (2007/10/02)
Elaboration of lactam (1), readily available from (L)-pyroglutamic acid, provides access to a range of 2,4- and 2,3,4-substituted pyrrolidinones.
