CHEMISTRY OF THE MICROBIAL METABOLITE A88696F, A NEW 2-(ALPHA-HYDROXYALKYL) TETRONIC ACID

Authors
BONJOUKLIAN R
Citation
R. Bonjouklian, CHEMISTRY OF THE MICROBIAL METABOLITE A88696F, A NEW 2-(ALPHA-HYDROXYALKYL) TETRONIC ACID, Tetrahedron letters, 34(49), 1993, pp. 7861-7864
Citations number
7
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron letters → ACNP
ISSN journal
00404039
Volume
34
Issue
49
Year of publication
1993
Pages
7861 - 7864
Database
ISI
SICI code
0040-4039(1993)34:49<7861:COTMMA>2.0.ZU;2-U
Abstract
Some unusual chemistry of the gastric ATP-ase inhibitor A88696F (3), a naturally-occurring 2-(alpha-hydroxyalkyl) tetronic acid, is describe d. It undergoes triethylamine-mediated reduction of the hydroxyl group to afford A88696C (1), presumably via the olefin 4. This olefin was p repared from 3 in high yield under mild acidic conditions, and was ste reoselectively rehydrated bade to alcohol 3, and epoxidized to A88696D (2).