A remarkably facile and stereochemically controlled fragmentation reaction in the hygrolide group of macrolide antibiotics

✍ Scribed by Stephen Hanessian; Ashok Tehim; Qingchang Meng; Kenneth Granberg

• Book ID: 104255904
• Publisher: Elsevier Science
• Year: 1996
• Tongue: French
• Weight: 194 KB
• Volume: 37
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(96)02113-2

✦ Synopsis

Treatment of bafilomycin A 1 and isobafilomycin A 1 with triphenylphosphine and diethylazodicarboxylate under Mitsunobu conditions led to a fragmentation of the sugar-like ring to give the corresponding olefinic ester. The structure of the product from bafilomycin At was confirmed by single crystal X-ray analysis and by 1H NMR.