Total Syntheses of Holomycin, Thiolutin, and Aureothricin

The reactions of 4-benzylthio-5-benzylthiomethyl-3-hydroxy-2-oxo-2,5-dihydrofuran with ammonia and primary amines gave 3-amino-4-benzylthio-5-benzylthiomethyl-3-pyrrolin-2-one derivatives. 3-Acylamino-4-benzylthio-5-benzylthiomethylene-3-pyrrolin-2-one derivatives, including the intermediate of the synthesis of holomycin by Buchi, were prepared by the treatment of the 3-acylaminolactams derived from the 3-aminolactams with chloranil or DDQ. Thiolutin and aureothricin were also synthesized from 3-acetamido- and 3-propionamido-4-benzylthio-5-benzylthiomethylene-1-methyl-3-pyrrolin-2-one respectively.