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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.
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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 | ||||
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Subjects: | Q Science > QD Chemistry | ||||
Journal or Publication Title: | TETRAHEDRON | ||||
Publisher: | PERGAMON-ELSEVIER SCIENCE LTD | ||||
ISSN: | 0040-4020 | ||||
Official Date: | 9 April 1993 | ||||
Dates: |
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Volume: | 49 | ||||
Number: | 15 | ||||
Number of Pages: | 20 | ||||
Page Range: | pp. 3165-3184 | ||||
Publication Status: | Published |
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