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Synthesis of both the enantiomers of methyl tuberonate 3, natural methyl β-d-glucopyranosyloxyjasmonate 6, and its epimer, methyl β-d-glucopyranosyl-tuberonate 5 is described. They were synthesized via mild deprotection of dichloroacetate and trifluoroacetate by methanolysis from the enantiomerically pure dithiane 9.
Both the enantiomers of methyl cis-(Z)-dehydrojasmonate 1 were prepared from the common intermediate 4 of our jasmonoid synthesis. (2S,3R)-1 was proved to be identical with the naturally occurring enantiomer by GC analysis using a chiral stationary phase.
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