Tetrahedron Letters, 26 October 2016, Vol.57(43), pp.4842-4844
Total synthesis of optically pure (+)-Fuligocandin A from -proline has been achieved in 29% overall yield. The key step, one-pot reductive cyclodehydration of the chiral 2-nitrophenyl-1,3-dicarbonyl compound, proceeds with 〉98% retention of configuration. This method represents a convenient approach to the synthesis of 2-methylenebenzo[ ][1,4]diazepin-5-ones containing one chiral center. A series of benzo[ ][1,4]diazepin-5-one derivatives have been successfully synthesized with retention of chirality by the one-pot reaction developed in this work. A possible reductive cyclodehydration mechanism was also proposed.
(+)-Fuligocandin ; 2-Methylenebenzo[E][1,4]Diazepin-5-One ; Vinylogous Amide ; One-Pot Reductive Cyclodehydration ; Chemistry
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