Entwicklung einer variationsfähigen Synthese für das Antibiotikum (+)-Thiolactomycin und für verwandte Thiotetronsäuren (English shop)

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Thiolactomycin, a thiotetronic acid natural product produced by the actinomycete strain Nocardia sp., represents an interesting synthetic target. On the one hand because of its activity, since thiolactomycin shows activity against Mycobacterium tuberculosis as well as against the malaria pathogen Plasmodium falciparum. In doing so, thiolactomycin affects bacterial fatty acid synthesis, but human fatty acid synthesis considerably less. On the other hand because of its structure, since, alongside its thiotetronic acid unit with the quaternary sulfur-containing stereocenter as well as the diene chain, thiolactomycin contains interesting structural elements. The key steps of the synthesis described here are the catalytic asymmetric Sharpless epoxidation of 2,4-pentadien-1-ols as well as a specially developed syn-selective SN’ thiolysis of the resulting allylic epoxides.