The aza-robinson annulation: An application to the synthesis of iso-A58365A

✍ Scribed by Francis G. Fang; Maurizio Prato; Guncheol Kim; Samuel J. Danishefsky

• Publisher: Elsevier Science
• Year: 1989
• Tongue: French
• Weight: 258 KB
• Volume: 30
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)80465-2

✦ Synopsis

Annulation of diazomethylvinylketone (4a) with a variety of secondary thiolactams provides a novel route to dihydro-y-pyridones.

This approach has been applied to the synthesis of iso-A58365A ( ), the y-pyridone analog of the ACE inhibitor, A58365A (1).

We have recently described a novel route to 5-hydroxy-2pyridones in the context of the total synthesis of the angiotensin converting enzyme (ACE) inhibitor, A58365A (1).2 In order to gain some insight into the structural features of 1 which are pertinent to its biological activity, the synthesis of several variants was undertaken. A particularly interesting target was the isomeric 4-pyridone (2). The biological evaluation of this (