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- Title
Short, Enantiospecific Syntheses of Indolizidines 209B and 209D, and Piclavine A from Diethyl- L-Glutamate.
- Authors
Jefford, Charles W.; Sienkiewicz, Krzysztof; Thornton, Steven R.
- Abstract
The 1 H-pyrrole derivative obtained from diethyl L-glutamate hydrochloride and tetrahydro-2,5-dimethoxyfuran was cyclized with BBr3 to ethyl (5 S)-5,6,7,8-tetrahydro-8-oxoindolizine-5-carboxylate ( 18). Catalytic hydrogenation of 18 over Pd/C in AcOH gave ethyl (5 S,8a R)-octahydroindolizine-5-carboxylate ( 21), whereas hydrogenation over Rh/Al2O3 in EtOH/AcOH 99:1 afforded mainly ethyl (5 S,8 S,8a S)-octahydro-8-hydroxyindolizine-5-carboxylate ( 22). By functional-group interconversions, 21 was transformed into piclavine A ( 1) and indolizidine 209D ( 2). Similarly, (5 R,8 R,8a S)-octahydro-5-pentylindolizine-8-methanol ( 37), the final relay for indolizidine 209B ( 3), was obtained from 22.
- Publication
Helvetica Chimica Acta, 1995, Vol 78, Issue 6, p1511
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19950780610