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https://hdl.handle.net/2440/4372
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Type: | Journal article |
Title: | Syntheses of angucyclinones related to ochromycinone |
Author: | Rozek, T. Janowski, W. Hevko, J. Tiekink, E. Dua, S. Stone, D. Bowie, J. |
Citation: | Australian Journal of Chemistry: an international journal for chemical science, 1998; 51(6):515-523 |
Publisher: | C S I R O PUBLICATIONS |
Issue Date: | 1998 |
ISSN: | 0004-9425 |
Statement of Responsibility: | Tomas Rozek, Wit Janowski, John M. Hevko, Edward R. T. Tiekink, Suresh Dua, David J. M. Stone and John H. Bowie |
Abstract: | Two synthetic approaches have been investigated for the syntheses of model angucyclinones related to ochromycinone. The first involves a Diels–Alder/Friedel–Crafts strategy in which the Diels–Alder adduct formed between dimethyl acetylenedicarboxylate and 3-ethenyl-5,5-dimethylcyclohex-2-en-1- one was converted into 6,6-dimethyl-8-oxo-5,6,7,8-tetrahydronaphthalene-1,2-dicarboxylic anhydride, which was then reacted with benzene in a Friedel–Crafts reaction. Acid-catalysed cyclization of the Friedel–Crafts products gave 3,3-dimethyl-3,4-dihydrobenz[a]anthracene-1,7,12(2H)-trione (3) in poor yield. Angucyclinones related to (3) are formed (in 40–50% overall yield) by aromatization of the adduct formed between the appropriate 1,4-naphthoquinone and 3-[(E)-2-methoxyethenyl]- 5,5-dimethylcyclohex-2-en-1-one (this dienone reacts with itself by a Diels–Alder process to yield an adduct which decomposes to 3,3,8,8-tetramethyl-3,4,7,8-tetrahydroanthracene-1,6(2H,5H)-dione). When the substituted 1,4-naphthoquinone is unsymmetrical, a boron triacetate assisted Diels–Alder reaction gives a single regioisomer (e.g. X-ray investigations indicate that 8-hydroxy-3,3-dimethyl-3,4-dihydrobenz[a]anthracene-1,7,12(2H)-trione is the product from 5-hydroxy-1,4-naphthoquinone). An X-ray structural study of the Diels–Alder adduct in the above reaction confirms the operation of an endo cyclization. |
DOI: | 10.1071/C97151 |
Published version: | http://dx.doi.org/10.1071/c97151 |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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