Abstract
A seven-step total synthesis of Hagen’s gland lactones 1 and 2 starting from 1,2- O-isopropylidene-α- d-xylofuranose 3 is reported. The success of this short and practical synthesis depends on the use of two key reactions: a stereoselective nucleophilic substitution at the anomeric position of 5 and 6, which allowed the construction of the γ-lactone ring, and an alkyl substitution reaction on tosylated compound 4, which permitted the carbon chain elongation of the tetrahydrofuran ring appendage at C-6.
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