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https://hdl.handle.net/2440/23536
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Type: | Journal article |
Title: | Utilization of a 1,2-dioxine for the synthesis of the four possible stereoisomers of oak lactone |
Author: | Brown, R. Taylor, D. Elsey, G. |
Citation: | Organic Letters, 2006; 8(3):463-466 |
Publisher: | Amer Chemical Soc |
Issue Date: | 2006 |
ISSN: | 1523-7060 1523-7052 |
Statement of Responsibility: | Rachel C. Brown, Dennis K. Taylor, and Gordon M. Elsey |
Abstract: | The natural products cis- and trans-oak lactone (1) have been prepared, along with their enantiomeric counterparts, from furanone 12, which was itself prepared from racemic 1,2-dioxine 9 and a chiral malonate diester. The key steps in the synthesis of 1 are the use of the malonate diester as a chromatographic resolving agent and the decarboxylation of 13, which can be directed to give either the cis- or trans-product. This leads to all four possible oak lactone stereoisomers from a common intermediate. |
Keywords: | Quercus Lactones Dioxins Biological Products Molecular Structure Stereoisomerism |
Description: | Copyright © 2006 American Chemical Society |
DOI: | 10.1021/ol052754u |
Published version: | http://pubs.acs.org/cgi-bin/abstract.cgi/orlef7/2006/8/i03/abs/ol052754u.html |
Appears in Collections: | Aurora harvest 2 Chemistry publications |
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