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Assembly of the TAN-1057 A/B Heterocycle from a Dehydroalanine Precursor
31 December 2000 (online)
A tandem reaction process was used to form the tetrahydropyrimidinone core of the TAN-1057 A and B dipeptide antibiotics. Michael addition of ammonia to a dehydroalanine derivative, followed by intramolecular displacement of an S-methylisothiourea assembles the tetrahydropyrimidinone in one-step.
amino acids - antibiotics - cyclizations - nucleophilic additions - tandem reactions