STEREOSELECTIVE SYNTHESIS OF TILIVALLINE

Authors
NAGASAKA T KOSEKI Y
Citation
T. Nagasaka et Y. Koseki, STEREOSELECTIVE SYNTHESIS OF TILIVALLINE, Journal of organic chemistry, 63(20), 1998, pp. 6797-6801
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Journal of organic chemistry → ACNP
ISSN journal
00223263
Volume
63
Issue
20
Year of publication
1998
Pages
6797 - 6801
Database
ISI
SICI code
0022-3263(1998)63:20<6797:SSOT>2.0.ZU;2-R
Abstract
Tilivalline 1, a metabolite from Klebsiella pneumoniae var. ocytoca, w as easily synthesized in five steps from (S)-proline and 3-(benzyloxy) isatoic anhydride 4g. This synthesis is based on modified Curtius reac tions of 3-substituted phthalic anhydrides 11 to 3-substituted isatoic anhydrides 4, conversion of lactams 6 to the acyliminium precursors 7 and stereoselective introduction of indole from the less hindered sid e of 7.