Abstract
Chemical means were used to achieve the epimerization at C-6 of 6α-eudesmanolides, with several functionalizations, to 7β-eudesmanolides. The process consists of the LiAlH 4 reduction of a 6α-lactone, selective acetylation of the hydroxymethylene group at C-12, oxidation and reduction at C-6 to epimerize this carbon, deacetylation at C-12 and final formation of a 6β-lactone with RuH 2(Ph 3P) 4. The whole process yields nearly 40% of the 6β-lactone, oxidation with the ruthenium reagent (58 and 53%) being the limiting step.
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