Syntheses of Angucyclinones Related to Ochromycinone. Part 3. 11-Hydroxy Isomers and Some Reduced Analogues
| dc.contributor.author | Rozek, T. | |
| dc.contributor.author | Taylor, D. | |
| dc.contributor.author | Tiekink, E. | |
| dc.contributor.author | Bowie, J. | |
| dc.date.issued | 1999 | |
| dc.description.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> | |
| dc.identifier.citation | Australian Journal of Chemistry, 1999; 52(2):129-135 | |
| dc.identifier.doi | 10.1071/C98124 | |
| dc.identifier.issn | 0004-9425 | |
| dc.identifier.issn | 1445-0038 | |
| dc.identifier.uri | http://hdl.handle.net/2440/4341 | |
| dc.language.iso | en | |
| dc.publisher | C S I R O PUBLISHING | |
| dc.source.uri | https://doi.org/10.1071/c98124 | |
| dc.title | Syntheses of Angucyclinones Related to Ochromycinone. Part 3. 11-Hydroxy Isomers and Some Reduced Analogues | |
| dc.type | Journal article | |
| pubs.publication-status | Published |