Abstract
Reduced derivatives of 2,3-seco-28-oxo-19,28-epoxy-18-olean-2,3-dicarboxylic acid and its cyclic anhydride were prepared. Reduction of the starting 2,3-secodicarboxylic acid by NaBH 4 –I 2 produced the 2,3-seco-2,3-dihydroxy derivative. Reaction of the starting anhydride with LiAlH 4 gave the 2,3-seco2,3,19,28-tetrahydroxy derivative. Cyclization using acidic reagents of the 2,3-seco-2,3-hydroxy- and 2,3seco-2,3,19,28-tetrahydroxy derivatives gave the corresponding cyclic ethers containing an oxepane ring. The anhydride ring was reduced by NaBH 4 to the corresponding -lactone, the structure of which was confirmed by an x-ray crystal structure.
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