Utilization of a 1,2-Dioxine for the Synthesis of the Four Possible Stereoisomers of Oak Lactone
- 4 January 2006
- journal article
- Published by American Chemical Society (ACS) in Organic Letters
- Vol. 8 (3) , 463-466
- https://doi.org/10.1021/ol052754u
Abstract
[reaction: see text]. 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
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