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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
Statement of
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
Biological Products
Molecular Structure
Description: Copyright © 2006 American Chemical Society
DOI: 10.1021/ol052754u
Published version:
Appears in Collections:Aurora harvest 2
Chemistry publications

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