Utilization of a 1,2-dioxine for the synthesis of the four possible stereoisomers of oak lactone.
[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.
Brown
Rachel C
RC
The Australian Wine Research Institute, Glen Osmond, South Australia 5064, Australia.
Taylor
Dennis K
DK
Elsey
Gordon M
GM
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D004147:Dioxins / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis*; D015394:Molecular Structure; D029963:Quercus / Q000737:chemistry*; D013237:Stereoisomerism
D001688:Biological Products; D004147:Dioxins; D007783:Lactones