Journal of the Chemical Society. Perkin transactions I p. 1046 - 1051 (1981)
Update date:2022-08-16
Topics:
Pattenden, Gerald
Whybrow, Derek
Synthetic routes to the E- and Z-cyclopentenones (20) and (25), which incorporate photosensitive 1,4-diene systems, are described.Irradiation of the E-cyclopentenone (20) is shown to result in efficient regiospecific di-?-methane rearrangement (>70percent) to the vinylcyclopropane (26), which is then converted into trans-deoxytaylorione (28).Irradiation of the corresponding Z-cyclopentenone (25) also leads to (26), presumably by way of the E-cyclopentenone (20), produced by Z-E photoisomerisation.
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