Please use this identifier to cite or link to this item: http://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, 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.
RMID: 0030002767
DOI: 10.1071/C97151
Appears in Collections:Chemistry publications

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