PROGRESS TOWARDS A PRACTICAL TOTAL SYNTHESIS OF CALABAR ALKALOIDS - TOTAL SYNTHESIS OF (-)-ESERMETHOLE AND (-)-PHYSOVENOL METHYL-ETHER FROM3S)-1,3-DIMETHYL-3-CARBOXYMETHYL-5-METHOXYOXINDOLE

Authors
YU QS LUO WM LI YQ BROSSI A
Citation
Qs. Yu et al., PROGRESS TOWARDS A PRACTICAL TOTAL SYNTHESIS OF CALABAR ALKALOIDS - TOTAL SYNTHESIS OF (-)-ESERMETHOLE AND (-)-PHYSOVENOL METHYL-ETHER FROM3S)-1,3-DIMETHYL-3-CARBOXYMETHYL-5-METHOXYOXINDOLE, Heterocycles, 36(6), 1993, pp. 1279-1285
Citations number
23
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Heterocycles → ACNP
ISSN journal
03855414
Volume
36
Issue
6
Year of publication
1993
Pages
1279 - 1285
Database
ISI
SICI code
0385-5414(1993)36:6<1279:PTAPTS>2.0.ZU;2-J
Abstract
Chemical resolution of the oxindoleacetic acid (7) with brucine in wat er yielded the acid (7a) of (3S)-absolute configuration. Acid (7a), in using conventional methods, was converted into nitrile (8a), lactone (9a) and amides (10a), and (11a) respectively. Amide (10a), on reducti on with LAH in refluxing THF, directly yielded (-)-esermethole (12a), and amide (11a) similarly gave (-)-N1-benzylnoresermethole (13a). Redu ction of ester (6a) with LAH in refluxing THF yielded (-)-physovenol m ethyl ether (14a).