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https://hdl.handle.net/2440/4341
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DC Field | Value | Language |
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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.identifier.citation | Australian Journal of Chemistry: an international journal for chemical science, 1999; 52(2):129-135 | - |
dc.identifier.issn | 0004-9425 | - |
dc.identifier.uri | http://hdl.handle.net/2440/4341 | - |
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.language.iso | en | - |
dc.publisher | C S I R O PUBLISHING | - |
dc.source.uri | http://dx.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 | - |
dc.identifier.doi | 10.1071/C98124 | - |
pubs.publication-status | Published | - |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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