Abstract
A general strategy for the formal synthesis of (−)- trans-kumausyne 1 via the bicyclic lactone (3a R,5 R,6a R)- 4 and total synthesis of (5 R)-Hagen’s gland lactones 2 and 3 via bicyclic lactone (3a R,5 S,6a R)- 5 starting from diacetone- d-glucose 6 is described. Syntheses of 4 and 5 were achieved by Wittig olefination–lactonization–Michael addition of the corresponding lactols 16 and 17, respectively.
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