dc.contributor.author |
Brimble, Margaret |
en |
dc.contributor.author |
Laita, Olivia |
en |
dc.contributor.author |
Robinson, James |
en |
dc.date.accessioned |
2011-09-19T00:06:15Z |
en |
dc.date.issued |
2006 |
en |
dc.identifier.citation |
TETRAHEDRON 62(13):3021-3027 27 Mar 2006 |
en |
dc.identifier.issn |
0040-4020 |
en |
dc.identifier.uri |
http://hdl.handle.net/2292/8044 |
en |
dc.description.abstract |
The uncatalyzed reaction of 2-tert-butyldimethylsilyloxythiophene 2 with 1,4-quinones bearing either an electron withdrawing acetyl or a carbomethoxy group at C-2, was investigated. No reaction was observed using 1,4-quinones 8 and 9 bearing an ester group at C-2 whereas use of 1,4-quinones 10 and 11 bearing an acetyl group at C-2 only provided low yields of the silyloxythiophenes 15 and 16 resulting from electrophilic substitution of the silyloxythiophene by the 1,4-quinone. Use of the Lewis acids InCl3, Cu(OTf)2 and BF3·Et2O were investigated in an effort to improve the yield of the desired annulation reaction. BF3·Et2O proved to be the optimum catalyst for the synthesis of thiolactone naphthofuran adducts 14 and 18 from 1,4-naphthoquinones 9 and 11, respectively. Reaction of 2-tert-butyldimethylsilyloxythiophene 2 with 1,4-benzoquinones 8 and 10 bearing a carbomethoxy or an acetyl group at C-2, respectively, afforded thiolactone benzofuran adducts 13 and 17, respectively, catalyzed by either InCl3 or Cu(OTf)2. Addition of 2-tert-butyldimethylsilyloxythiophene 2 to 3-acetyl-5-methoxy-1,4-naphthoquinone 12 afforded adduct 19 that underwent oxidative rearrangement to thiolactone pyranonaphthoquinone 20 using ceric ammonium nitrate in acetonitrile, thus providing a novel approach for the synthesis of a thia analogue of the pyranonaphthoquinone antibiotic kalafungin. |
en |
dc.language |
EN |
en |
dc.publisher |
Elsevier Ltd. |
en |
dc.relation.ispartofseries |
Tetrahedron |
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. Details obtained from http://www.sherpa.ac.uk/romeo/issn/0040-4020/ |
en |
dc.rights.uri |
https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm |
en |
dc.subject |
silyfoxythiophene |
en |
dc.subject |
quinones |
en |
dc.subject |
pyranonaphthoquinone antibiotics |
en |
dc.subject |
annulation |
en |
dc.subject |
CATALYZED CONJUGATE ADDITION |
en |
dc.subject |
ELECTRON-DEFICIENT OLEFINS |
en |
dc.subject |
PYRANONAPHTHOQUINONE ANTIBIOTICS |
en |
dc.subject |
VINYLOGOUS MANNICH |
en |
dc.subject |
SYNTHETIC UTILITY |
en |
dc.subject |
2-SILYLOXY DIENES |
en |
dc.subject |
ALDOL REACTION |
en |
dc.subject |
PYRROLE |
en |
dc.subject |
FURAN |
en |
dc.title |
Addition of 2-tert-Butyldimethylsilyloxythiophene to Activated Quinones: An Approach to Thia Analogues of Kalafungin |
en |
dc.type |
Journal Article |
en |
dc.identifier.doi |
10.1016/j.tet.2006.01.040 |
en |
pubs.issue |
13 |
en |
pubs.begin-page |
3021 |
en |
pubs.volume |
62 |
en |
dc.rights.holder |
Copyright: 2006 Elsevier Ltd. |
en |
pubs.end-page |
3027 |
en |
dc.rights.accessrights |
http://purl.org/eprint/accessRights/RestrictedAccess |
en |
pubs.subtype |
Article |
en |
pubs.elements-id |
49010 |
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 |