Sternbach-Goldberg

Goldberg-Sternbach approach, by the treatment with hydrochloric acid (HCl) (Fig. (5)) [55]. The optical resolution of rac-13 with natural... 

One of the most practical approaches among those described in Fig. (4) involves optical resolution of hydroxylactone rac-13, which is readily derived from acetoxylactone rac-1, an intermediate of Goldberg-Sternbach approach, by the treatment with hydrochloric acid (HC1) (Fig. (5)) [55]. The optical resolution of rac-13 with natural... 

In 1946, Moses W. Goldberg (1905-1964) and Leo H. Sternbach from Hoffmann-La Roche filed the first of several patent applications relating to the synthesis of biotin (Fig. 7.48). The starting material was fumaric acid, which was tra/is-dibrominated. NucleophEic substitution with benzylamine, cyclisation with phosgene and treatment with acetic anhydride gave the cis-substituted meso-imidazolidinone, which was converted with cydohexanol into the halfester. The enantiomers were then separated with (-)-ephedrine. Alternatively,... 

The industrial synthesis of Goldberg and Sternbach (Hoffmann-La Roche) was a landmark achievement, which allowed for the first time to produce enantiomericaUy pure biotin in large quantities. 

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