Journal of the Chemical Society. Perkin transactions I p. 3149 - 3154 (1988)
Update date:2022-08-11
Topics:
Harapanhalli, Ravi S.
The synthesis of an eudesmanic alcohol, kudtriol (1), is described along with its 11-deoxy analogue (19) starting from 1-(α)-santonin in ten steps.The known intermediate methyl (11S)-3-oxoeudesm-4-en-12-oate (5b) was taken through the new intermediates methyl (11S)-eudesm-4-en-12-oate (6), (11S)-eudesm-4-en-12-al (17), 11-hydroxyeudesm-4-en-12-al (18), and eudesm-4-ene-11,12-diol (8).The consstruction of side-chain diol moiety in the last mentioned intermediate was achieved by the application of Vedejs' enolate hydroxylation on (17).The sensitized photo-oxygenation cum reduction sequence transformed the ene diol (8) into the title compound (1).A similar sequence on (11S)-eudesm-4-en-12-ol (16) resulted in 11-deoxykudtriol (19).
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