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| Title: | Synthesis and stereochemical assignment of (+)-chamuvarinin |
| Authors: | Florence, Gordon John
Morris, Joanne Charleen
Murray, Ross George
Osler, Jonathan
Reddy, Vanga R.
Smith, Terry K |
| Keywords: | Hydrolytic kinetic resolution
Annonaceous acetogenins
Uvaria-chamae
Stereoisomer library
Recent progress
Mosher method
Bearing
Condensation
Mechanisms
Murisolins
QD Chemistry |
| Issue Date: | 4-Feb-2011 |
| Citation: | Florence , G J , Morris , J C , Murray , R G , Osler , J , Reddy , V R & Smith , T K 2011 , ' Synthesis and stereochemical assignment of (+)-chamuvarinin ' Organic Letters , vol 13 , no. 3 , pp. 514-517 . |
| Abstract: | A stereocontrolled total synthesis of (+)-chamuvarinin, isolated from the root extract of Uvaria Chamae, utilizes a convergent modular strategy to construct the adjacently linked C15−C28 ether array, followed by a late-stage Julia−Kocienski olefination to append the butenolide motif. This constitutes the first total synthesis of (+)-chamuvarinin, defining the relative and absolute configuration of this unique annonaceous acetogenin. |
| Version: | Publisher PDF |
| Description: | Supported by grants from EPSRC (EP/F011458/1) and The Wellcome Trust (086658). |
| Status: | Peer reviewed |
| URI: | http://hdl.handle.net/10023/1685 |
| DOI: | http://dx.doi.org/10.1021/ol1028699 |
| ISSN: | 1523-7060 |
| Type: | Journal article |
| Rights: | (c)2011 American Chemical Society. This article is open access under the ACS AuthorChoice option. |
| Appears in Collections: | Biomedical Sciences Research Complex (BSRC) Research
University of St Andrews Research
Biology Research
Chemistry Research
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