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MODEL STUDIES RELATED TO THE TOTAL SYNTHESIS OF THE FUMITREMORGINS - THE PICTET-SPENGLER CYCLIZATION AND THE FORMATION AND INTRAMOLECULAR ACYLATION OF A 1,2-DIHYDRO-BETA-CARBOLINE DERIVATIVE
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UNSPECIFIED (1993) MODEL STUDIES RELATED TO THE TOTAL SYNTHESIS OF THE FUMITREMORGINS - THE PICTET-SPENGLER CYCLIZATION AND THE FORMATION AND INTRAMOLECULAR ACYLATION OF A 1,2-DIHYDRO-BETA-CARBOLINE DERIVATIVE. TETRAHEDRON, 49 (15). pp. 3165-3184. ISSN 0040-4020
Full text not available from this repository.Abstract
The preparations of the tetrahydro-beta-carbolines 8, 9b, and 9d are described. The Pictet-Spengler reaction of L-tryptophyl-L-proline methyl ester with 3-methylbutanal gave the tetrahydro-beta-carbolines 20 and 21; subsequent acid-catalysed cyclisation afforded the fumitremorgin analogues 22 and 23. The 2-(p-toluenesulphonyl)tetrahydro-beta-carboline 27a furnished the unsaturated pentacycle 28a upon treatment with alkali.
| Item Type: | Journal Article |
|---|---|
| Subjects: | Q Science > QD Chemistry |
| Journal or Publication Title: | TETRAHEDRON |
| Publisher: | PERGAMON-ELSEVIER SCIENCE LTD |
| ISSN: | 0040-4020 |
| Date: | 9 April 1993 |
| Volume: | 49 |
| Number: | 15 |
| Number of Pages: | 20 |
| Page Range: | pp. 3165-3184 |
| Publication Status: | Published |
| URI: | http://wrap.warwick.ac.uk/id/eprint/21396 |
Data sourced from Thomson Reuters' Web of Knowledge
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