Structure of Chlorodesoxypatulinic Acid
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.
An efficient total synthesis of the antibiotic patulin
Abstract The potent antibiotic patulin (1) has been synthesized in six steps (41.3% overall yield) from 2-(tert-butyldimethylsilyloxy)-4-[(tert-butyldimethylsilyloxy)-methyl]furan (2) and benzyloxyacetaldehyde (4).
Highly enantio- and diastereoselective synthesis of β-methyl-γ-monofluoromethyl-substituted alcohols.
Enanatiopure β-methyl-γ-monofluoromethyl alcohols were prepared from the allylic alkylation between fluorobis(phenylsulfonyl)methane with Morita-Baylis-Hillman carbonates. The reaction was catalyzed by using the Cinchona alkaloid derivative, (DHQD)(2)AQN. The origin of the stereoselectivity was verified by DFT methods. Calculated geometries and relative energies of various transition states strongly support the observed stereoselectivity.