Synthesis of (-)-bactobolin from D-glucose and from (+)-actinobolin

✍ Scribed by Dale E. Ward; Yuanzhu Gai; Brian F. Kaller

• Book ID: 104214438
• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 309 KB
• Volume: 35
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)73216-3

✦ Synopsis

The preparation of (-)-16 from (+)-3 constitutes a formal enuntiospecific synthesis of (-)-bactobotin from D-glucose. The key traasfonnation involves the diustereoselective addition of LiCHCl2 to 7 in the presence of CeC13. The synthesis of (+)-3 from (+)-uctinobolin sulfate is reported and illustrates the conversion of (+)-uctinobolin into (-)-bactobolin. Bactobolin (l),] a metabolite of Pseudomonas yoshiafomiensis, is a broad spectrum antibiotic and has