dc.contributor.author |
Brimble, Margaret |
en |
dc.contributor.author |
Stuart, SJ |
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dc.date.accessioned |
2011-09-19T21:28:04Z |
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dc.date.issued |
1990-01 |
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dc.identifier.citation |
J CHEM SOC PERK T 1 881-885 Apr 1990 |
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dc.identifier.issn |
0300-922X |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8143 |
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dc.description.abstract |
The syntheses of 5-epi-7-deoxykalafungin (12a) and 5-epi-7-o-methylkalafungin (12b), compounds closely related to the pyranonaphthoquinone antibiotic kalafungin (1), have been completed making use of the transformation of one tricyclic ring system into another. The uncatalysed 1,4-addition of 2-trimethylsilyloxyfuran (4) to the 2-acetyl-1,4-naphthoquinones (8) gave the furo[3,2-b]naphtho[2,1 -d]furans (9) which underwent facile oxidative rearrangement in 72–76% yield using cerium(IV) ammonium nitrate, to the furo[3,2-b]naphtho[2,3-d]pyrans (11) which contain the same ring system as the natural product kalafungin (1). Reduction of the hemiacetals (11) to the cyclic ethers (12) was effected using triethylsilane in trifluoroacetic acid. The analogous rearrangement of the furo[3,2-b]benzofuran (5a) to the furo[3,2-b][2]benzopyran (6) proceeded in only 27% yield. Further insight into the mechanism of the initial 1,4-addition reaction was gained by isolation of the intermediate (13) in the reaction of 2-trimethylsilyloxyfuran (4) with the naphthoquinone (8a). |
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dc.language |
aa |
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dc.relation.ispartofseries |
Journal of the Chemical Society, Perkin Transactions 1 |
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dc.rights |
Items in ResearchSpace are protected by copyright, with all rights reserved, unless otherwise indicated. Previously published items are made available in accordance with the copyright policy of the publisher. |
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dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
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dc.title |
Synthesis of 5-epi-7-deoxykalafungin and 5-epi-7-O-methylkalafungin |
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dc.type |
Journal Article |
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dc.identifier.doi |
10.1039/P19900000881 |
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pubs.issue |
4 |
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pubs.begin-page |
881 |
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dc.rights.holder |
Copyright: 1990 Royal Society of Chemistry |
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pubs.end-page |
885 |
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dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
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pubs.subtype |
Article |
en |
pubs.elements-id |
141836 |
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pubs.org-id |
Science |
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pubs.org-id |
Chemistry |
en |
pubs.org-id |
Science Research |
en |
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
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dc.identifier.eissn |
1364-5463 |
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pubs.record-created-at-source-date |
2013-04-15 |
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