Olivomycin and related antibiotics XXV. Stereochemistry of the side chain of olivin

Summary The configurations of the C₃ and C₄ centers of olivin have been shown by the oxidative cleavage of olivin penta- and hexaacetates (V) and (VI) with the formation of D-acetyllactic and D-threo-dihydroxy-butyric acids (VIII) and (IX). The stereochemistry of the C₁ center has been determined by the spectropolarimetric correlation of the products of the degradation of olivin (XVI)–(XVIII) with the model substances (XXII)–(XXIV). As a result, the 2S, 3R, 1S, 3S, 4R configuration has been established for olivin.For Communications XXIII and XXIV, see [1, 2]; for a preliminary communication, see [3].M. M. Shemyakin Institute of the Chemistry of Natural Compounds, Academy of Sciences of the USSR. Translated from Khimiya Prirodnykh Soedinenii, No. 4, pp. 519–525, July–August, 1972.