Abstract
AbstractWe have synthesized (±)‐loliolide (7 a), (±)‐actinidiolide (11 a), (±)‐dihydroactinidiolide (16), and (±)‐isodihydroactinidiolide (18) through various reaction paths starting from homosafranic acid (4 a). Thus, (±)‐actinidiolide has been synthesized for the first time, and this result allows to discard the alternative formula 11 b for that compound [2].By investigation of the sensitized photooxygenation of methyl homosafranate (4 b), this reaction is shown to lead to an interesting spiro‐peroxylactone 25, beside the expected endo‐peroxide 23. Specific oxygenation of the tetrasubstituted double bond of methyl homosafranate, and cyclisation of the hydroperoxide 24 thus produced, are believed to account for the formation of such a particular compound.The base‐catalysed rearrangement of the endo‐peroxide 23 gives rise to two compounds, one being the expected keto‐hydroxy‐ester 26. The other ‐ to which is assigned the glycidic ester structure 27 ‐ obviously results from an internal displacement reaction on oxygen in 23. It is note‐worthy that the sensitized photooxygenation of methyl homosafranate proceeds directly to the same glycidic ester when it is carried out in an alcaline solution.
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