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Letters to Nature
Nature 165, 928-930 (10 June 1950) | doi:10.1038/165928b0
Structure of Chlorodesoxypatulinic Acid
R. B. WOODWARD & GURBAKHSH SINGH
- Converse Memorial Laboratory, Harvard University. Jan. 31.
Abstract
BERGEL et al.1 found that the product of the action of ethanolic hydrogen chloride on patulin gave on hydrolysis a crystalline chloro-acid, C7H7O4Cl, now called Chlorodesoxypatulinic acid. Afterwards, Plattner et al.2 observed that the same acid was readily produced by the action of hydrogen chloride on patulin in moist ethereal solution. The expression (I) was originally deduced1 for Chlorodesoxypatulinic acid from its relationship to patulin, for which the structure (II) was assumed3. Recent developments in this Laboratory and in that of Plattner necessitated the abandonment of these views, and led the Swiss group2 to formulate Chlorodesoxypatulinic acid as (III), which was consonant with either of two new structures, (IV)4 and (V)2, put forward for patulin in Cambridge and in Zurich, respectively. We have now accumulated new evidence which requires that (III) in its turn be rejected, and which leads to a new view of the structure of chlorodesoxypatulinic acid which is consistent only with the structure (IV) for patulin.
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