dc.contributor.author |
Brimble, Margaret |
en |
dc.contributor.author |
Duncalf, Letecia |
en |
dc.contributor.author |
Neville, D |
en |
dc.date.accessioned |
2011-09-19T02:20:37Z |
en |
dc.date.issued |
1998 |
en |
dc.identifier.citation |
Journal of the Chemical Society, Perkin Transactions 1 (24): 4165-4173, 1998 |
en |
dc.identifier.issn |
1470-4358 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8089 |
en |
dc.description.abstract |
The preparation of bis-naphthoquinone 7, a key intermediate in the synthesis of dimeric pyranonaphthoquinones related to the actinorhodins is described. Initial efforts directed to 7 which focussed on a double Fries rearrangement of bis-acetate 14 to 2-acetylnaphthol 13 were low yielding. Use of a Stille coupling reaction between dimeric bromonaphthalene 20 and (α-ethoxyvinyl)tri-n-butyltin 19 as a means to introduce the acetyl groups at C-2 was also low yielding. The optimum route to bis-naphthoquinone 7 involved the synthesis of 2-acetylnaphthol 13 from bromide 25 using a Suzuki–Miyaura coupling. Addition of 2-trimethylsilyloxyfuran to bis-naphthoquinone 7 afforded the bis-annulation adducts 30,31 which underwent double oxidative rearrangement to bis-lactols 32,33. Reduction of the bis-lactols to bis-ethers 34,35 completed the first synthesis of a dimeric pyranonaphthoquinone. |
en |
dc.language |
EN |
en |
dc.relation.ispartofseries |
Journal of the Chemical Society, Perkin Transactions 1 |
en |
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. |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
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dc.subject |
CROSS-COUPLING REACTION |
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dc.subject |
NATURALLY-OCCURRING QUINONES |
en |
dc.subject |
ARYLBORONIC ACIDS |
en |
dc.subject |
ORGANOBORON COMPOUNDS |
en |
dc.subject |
EFFICIENT SYNTHESIS |
en |
dc.subject |
PALLADIUM |
en |
dc.subject |
HALOARENES |
en |
dc.subject |
ACTINORHODIN |
en |
dc.subject |
DERIVATIVES |
en |
dc.subject |
ACETYLATION |
en |
dc.title |
Double furofuran annulation to a bis-naphthoquinone: an approach to dimeric pyranonaphthoquinones |
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dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1039/A805031G |
en |
pubs.issue |
24 |
en |
pubs.begin-page |
4165 |
en |
dc.rights.holder |
Copyright: 1998 Royal Society of Chemistry |
en |
pubs.end-page |
4173 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
1098 |
en |
pubs.org-id |
Science |
en |
pubs.org-id |
Chemistry |
en |
pubs.org-id |
Science Research |
en |
pubs.org-id |
Maurice Wilkins Centre (2010-2014) |
en |
pubs.record-created-at-source-date |
2010-09-01 |
en |