Asymmetric synthesis of (-)-(R)-pyrrolam A starting from (S)-malic acid

Authors
Huang, PQ Chen, QF Chen, CL Zhang, HK
Citation
Pq. Huang et al., Asymmetric synthesis of (-)-(R)-pyrrolam A starting from (S)-malic acid, TETRAHEDR-A, 10(19), 1999, pp. 3827-3832
Citations number
24
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
TETRAHEDRON-ASYMMETRY
ISSN journal
09574166 → ACNP
Volume
10
Issue
19
Year of publication
1999
Pages
3827 - 3832
Database
ISI
SICI code
0957-4166(19990924)10:19<3827:ASO(AS>2.0.ZU;2-5
Abstract
An asymmetric synthesis of natural (-)-pyrrolam A starting from natural (S) -malic acid is described. The stereogenic center was established via a high ly trans-diastereoselective reductive alkylation procedure. A tandem base-i nduced intramolecular amide N-substitution and tosic acid elimination led t o the target molecule. (C) 1999 Elsevier Science Ltd. All rights reserved.