Abstract
A synthesis of lamberlianic acid 2a starting from podocarpic acid is described. The central intermediate, diester-ketone 4b, is obtained by ozonolysis and hydrogenation, and the exocyclic methylene group in ring B generated via a Reformatsky reaction. The furan ring is attached by nucleophilic attack of 3-lithiofuran, for which an improved preparation is described, on either the acid chloride 7b or the aldehyde 16. The 12-oxygen atom is removed by mesylation of the alcohols 12a and b and Li–liquid ammonia reduction.
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