Enantioselective and Diastereoselective Total Synthesis of the Antimycotically Active Natural Product Chlorotetaine: Revision of the Relative Configuration

With the bislactim ether method, followed by deprotonation with a chiral base the enantio- and diastereoselective construction of the unusual C-terminal amino acid of the dipeptide, chlorotetain (1) isolated from Bacillus subtilis, was achieved. Chlorotetain has an (S) configuration at the cyclohexenyl residue of the side chain, which contradicts the assignment reported in the literature.