Heteroatom-directed reverse Wacker oxidations. Synthesis of the reported structure of (-)-herbaric acid.

Choi, Peter; Sperry, Jonathan; Brimble, Margaret

dc.contributor.author	Choi, Peter	en
dc.contributor.author	Sperry, Jonathan	en
dc.contributor.author	Brimble, Margaret	en
dc.coverage.spatial	United States	en
dc.date.accessioned	2011-09-18T21:45:35Z	en
dc.date.issued	2010	en
dc.identifier.citation	J Org Chem 75(21):7388-7392 05 Nov 2010	en
dc.identifier.issn	0022-3263	en
dc.identifier.uri	http://hdl.handle.net/2292/7981	en
dc.description.abstract	A microwave-assisted chemoenzymatic resolution has been used to install the C3 stereocenter of the reported structure of the fungal metabolite herbaric acid in high enantiomeric excess. The synthesis and stereochemical assignment was accomplished using a completely regioselective anti-Markovnikov addition of water to vinylphthalide 3, achieved using a heteroatom-directed Wacker oxidation that proceeds with retention of stereochemistry. These results establish that so-called "reverse" Wacker oxidations are a viable alternative to hydroboration/oxidation procedures.	en
dc.language	eng	en
dc.publisher	The American Chemical Society	en
dc.relation.ispartofseries	The Journal of Organic Chemistry	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/0022-3263/	en
dc.rights.uri	https://researchspace.auckland.ac.nz/docs/uoa-docs/rights.htm	en
dc.subject	Biological Products	en
dc.subject	Fungi	en
dc.subject	Heterocyclic Compounds, 2-Ring	en
dc.subject	Lactones	en
dc.subject	Oxidation-Reduction	en
dc.subject	Stereoisomerism	en
dc.subject	Substrate Specificity	en
dc.title	Heteroatom-directed reverse Wacker oxidations. Synthesis of the reported structure of (-)-herbaric acid.	en
dc.type	Journal Article	en
dc.identifier.doi	10.1021/jo1016585	en
pubs.issue	21	en
pubs.begin-page	7388	en
pubs.volume	75	en
dc.rights.holder	Copyright: 2010 American Chemical Society	en
dc.identifier.pmid	20873747	en
pubs.end-page	7392	en
dc.rights.accessrights	http://purl.org/eprint/accessRights/RestrictedAccess	en
pubs.subtype	Article	en
pubs.elements-id	159696	en
pubs.org-id	Medical and Health Sciences	en
pubs.org-id	Medical Sciences	en
pubs.org-id	Auckland Cancer Research	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	2011-06-30	en
pubs.dimensions-id	20873747	en