Abstract
THE butanolide structure proposed by Clemo and Cocker1 for desmotropo-ψ-santonin (II) [p. 289], which is formed by the action of warm 55 per cent sulphuric acid on ψ-santonin, has been confirmed (compare Cocker and Lipman2). An intermediate compound in this transformation is now named ψ-santonic acid, to which structure (III) is tentatively assigned. Assuming that the most likely structure for ψ-santonin is (I), the conversion of this to (II) involves the destruction of asymmetry at C1, C5 and C10. In addition, C8 and C9 will also be affected during the reduction of ring B, which probably takes place by bond migration. By the nature of the acidic reagent involved in the re-arrangement, it is most unlikely that the configuration of C11 will be affected. Hence the conversion of ψ-santonin to desmotropo-ψ-santonin should lead to two pairs of diastereoisomers in both of which the configuration of C11 should be the same, Two of the latter should have the cis configuration and the other two the trans configuration at C8—C9.
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References
Clemo and Cocker, J. Chem. Soc., 30 (1946).
Cocker and Lipman, J. Chem. Soc., 533 (1947).
Huang Minlon Lo, and Chu, J. Amer. Chem. Soc., 65, 1780 (1943). Huang Minlon, J. Amer. Chem. Soc., 70, 611 (1948).
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COCKER, W., CROSS, B. & LIPMAN, C. Desmotropo-ψSantonins. Nature 163, 288–289 (1949). https://doi.org/10.1038/163288a0
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DOI: https://doi.org/10.1038/163288a0
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