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https://hdl.handle.net/2440/4341
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Type: | Journal article |
Title: | Syntheses of Angucyclinones Related to Ochromycinone. Part 3. 11-Hydroxy Isomers and Some Reduced Analogues |
Author: | Rozek, T. Taylor, D. Tiekink, E. Bowie, J. |
Citation: | Australian Journal of Chemistry: an international journal for chemical science, 1999; 52(2):129-135 |
Publisher: | C S I R O PUBLISHING |
Issue Date: | 1999 |
ISSN: | 0004-9425 |
Abstract: | <jats:p> The boron triacetate assisted Diels Alder reaction between racemic 5,5-dimethyl-3-vinylcyclohex- 2-enyl acetate and 5-hydroxynaphthoquinone yields the racemic 11-hydroxy-3,3-dimethyl-7,12-dioxo- 1,2,3,4,6,6a,7,12,12a,12b-decahydrobenzo[a]anthracen-1-yl acetate as the sole stereoisomer by regio- and stereo-selective cis endo addition. Aromatization of the Diels Alder adduct followed by hydrolysis of the acetate and oxidation of the resultant 1-hydroxy group gives the target angucyclinone, 11-hydroxy-3,3-dimethyl-1,2,3,4,7,12-hexahydrobenzo[a]anthracene-1,7,12-trione, in an overall yield of 37% from 5-hydroxynaphthoquinone. The regio- and stereo-selectivity of the Diels Alder addition is confirmed by a combination of 13C n.m.r. spectroscopy and X-ray crystallography.</jats:p> |
DOI: | 10.1071/C98124 |
Published version: | http://dx.doi.org/10.1071/c98124 |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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