SYNTHESIS OF A PYRANONAPHTHOQUINONE-SPIROACETAL

Brimble, Margaret; NAIRN, M

dc.contributor.author	Brimble, Margaret	en
dc.contributor.author	NAIRN, M	en
dc.date.accessioned	2011-09-19T21:51:36Z	en
dc.date.issued	1992-03	en
dc.identifier.citation	J CHEM SOC PERK T 1 579-583 Mar 1992	en
dc.identifier.issn	0300-922X	en
dc.identifier.uri	http://hdl.handle.net/2292/8157	en
dc.description.abstract	A synthesis of pyranonaphthoquinone-spiroacetal 12 is reported which represents an efficient entry to the pentacyclic framework of the pyranonaphthoquinone antibiotic griseusin A. The key step involves assembly of the furo[3,2-b]naphtho[2,3-d]pyran 11via a ceric ammonium nitrate oxidative rearrangement of the furo[3,2-b]naptho[2,1-d]furan 10. This latter heterocycle 10 in turn was constructed via the uncatalysed 1,4-addition of 2-trimethylsilyloxyfuran 9 to naphthoquinone 8. Naphthoquinone 8 is readily available from 1,4-dimethoxynaphthalene-2-carbaldehyde 3 and acetylene 4.	en
dc.language	EN	en
dc.publisher	ROYAL SOC CHEMISTRY	en
dc.relation.ispartofseries	J CHEM SOC PERK T 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	en
dc.subject	GRISEUSIN-A	en
dc.subject	ABSOLUTE-CONFIGURATION	en
dc.subject	ANTIBIOTICS	en
dc.title	SYNTHESIS OF A PYRANONAPHTHOQUINONE-SPIROACETAL	en
dc.type	Journal Article	en
dc.identifier.doi	10.1039/P19920000579	en
pubs.issue	5	en
pubs.begin-page	579	en
dc.rights.holder	Copyright: Royal Society of Chemistry	en
pubs.end-page	583	en
dc.rights.accessrights	http://purl.org/eprint/accessRights/RestrictedAccess	en
pubs.subtype	Article	en
pubs.elements-id	141827	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	2011-09-20	en