Asymmetric Synthesis of (+)-Galbelgin, (−)-Kadangustin J, (−)-Cyclogalgravin and (−)-Pycnanthulignenes A and B, Three Structurally Distinct Lignan Classes, Using a Common Chiral Precursor

Rye, C; Barker, David

dc.contributor.author	Rye, C	en
dc.contributor.author	Barker, David	en
dc.date.accessioned	2011-10-05T03:03:19Z	en
dc.date.accessioned	2011-10-06T23:57:22Z	en
dc.date.issued	2011	en
dc.identifier.citation	The Journal of Organic Chemistry 76(16):6636-6648 2011	en
dc.identifier.issn	0022-3263	en
dc.identifier.uri	http://hdl.handle.net/2292/8339	en
dc.description.abstract	The enantioselective synthesis of three structurally distinct classes of lignan from a single, aza-Claisen-derived, chiral morpholine amide is reported. The class of lignan formed is dependent on the substitution pattern in the aryl rings and choice of protecting group on a key benzylic hydroxyl group. The methodology has been used to asymmetrically synthesize and determine the absolute stereochemistry of lignans (+)-cyclogalgravin 3, (−)-pycnanthulignene A 4, (−)-pycnanthulignene B 5, and (−)-kadangustin J 8.	en
dc.language	EN	en
dc.publisher	American Chemical Society	en
dc.relation.ispartofseries	Journal of Organic Chemistry	en
dc.relation.replaces	http://hdl.handle.net/2292/8320	en
dc.relation.replaces	2292/8320	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	AZA-CLAISEN REARRANGEMENT	en
dc.subject	N-MONOSUBSTITUTED AMIDES	en
dc.subject	NATURAL-PRODUCTS	en
dc.subject	STEREOSELECTIVE-SYNTHESIS	en
dc.subject	TETRAHYDROFURAN LIGNANS	en
dc.subject	BENZODIOXANE NEOLIGNANS	en
dc.subject	HOLOSTYLIS-RENIFORMIS	en
dc.subject	EFFICIENT METHOD	en
dc.subject	(+)-TALAUMIDIN	en
dc.subject	ANGUSTIFOLIA	en
dc.title	Asymmetric Synthesis of (+)-Galbelgin, (−)-Kadangustin J, (−)-Cyclogalgravin and (−)-Pycnanthulignenes A and B, Three Structurally Distinct Lignan Classes, Using a Common Chiral Precursor	en
dc.type	Journal Article	en
dc.identifier.doi	10.1021/jo200968f	en
pubs.issue	16	en
pubs.begin-page	6636	en
pubs.volume	76	en
dc.rights.holder	Copyright: AMER CHEMICAL SOC	en
dc.identifier.pmid	21749139	en
pubs.end-page	6648	en
dc.rights.accessrights	http://purl.org/eprint/accessRights/RestrictedAccess	en
pubs.subtype	Article	en
pubs.elements-id	219675	en
pubs.org-id	Science	en
pubs.org-id	Chemistry	en
dc.identifier.eissn	1520-6904	en
pubs.record-created-at-source-date	2011-08-24	en
pubs.dimensions-id	21749139	en