A convenient synthesis of chiral 2-methylenebenzo[e][1,4]diazepin-5-ones via a one-pot reductive cyclodehydration with retention of chirality

作者：Sorra Kumaraswamy; Lai Chin Hung; Feng Chun Yen; Wu Yang Chang; Pusuluri Srinivas; Mukkanti Khagga; Chuang Ta Hsien^*

来源：Tetrahedron Letters, 2016, 57(43): 4842-4844.

DOI：10.1016/j.tetlet.2016.09.060

• (+)-Fuligocandin
• 2-Methylenebenzo[e][1,4]diazepin-5-one
• Vinylogous amide
• One-pot reductive cyclodehydration

Total synthesis of optically pure (+)-Fuligocandin A from L-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[e][1,4]diazepin-5-ones containing one chiral center. A series of benzo[e] [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.

• 出版日期2016-10-26
• 单位中国医科大学