A concise synthesis of AG5473/5507 utilizing N-acyliminium ion chemistry

✍ Scribed by Chuangxing Guo; Siegfried Reich; Rich Showalter; Ernie Villafranca; Liming Dong

• Book ID: 104210522
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 180 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00846-7

✦ Synopsis

FKBP-12 inhibitors AG5473 and AG5507 were resynthesized through a more ecient 11-step sequence.

The key steps involved propargyl trimethylsilane addition to an N-acyliminium ion, ozonolysis of the allene and acid-catalyzed cyclization. A mild protocol for introducing a formaldehyde moiety to an anomeric center was established. The synthetic materials were evaluated in the FKBP rotamase assay.