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.

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.

1. Bergel , Morrison , Moss and Binderknecht , J. Chem. Soc., 415 (1944).
2. Engel , Brzeski and Plattner , Helv. Chim. Acta, 32, 1166 (1949). | Article | ISI | ChemPort |
3. Raistrick , Birkenshaw , Michael and Bracken , Lancet, 245, 625 (1943).
4. Woodward and Singh , J. Amer. Chem. Soc., 71, 758 (1949); Experientia (in the press). | Article | ISI | ChemPort |