| Abstract
| - The completion of the total synthesis of thiostrepton (1) is described. The synthesis proceededfrom key building blocks 2−5, which were assembled into a growing substrate that finally led to the targetmolecule. Thus, the dehydropiperidine peptide core 2 was, after appropriate manipulation, coupled to thethiazoline−thiazole fragment 3, and the resulting product was advanced to intermediate 11 possessing thethiazoline−thiazole macrocycle. The bis-dehydroalanine tail equivalent 4 and the quinaldic acid fragment5 were then sequentially incorporated, and the products so obtained were further elaborated to forge thesecond macrocycle of the molecule. Several roadblocks encountered along the way were systematicallyinvestigated and overcome, finally opening the way, through intermediates 20, 32, 44, 45, and 46, to thetargeted natural product, 1.
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