Aldol condensation reactions of tricarbonyliron complexes. Towards building blocks for the synthesis of carbomycin B/tylosin macrolide antibiotics and fluorinated analogs

✍ Scribed by Michel Franck-Neumann; Philippe Geoffroy; Fabien Gumery

• Book ID: 104210333
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 183 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00569-4

✦ Synopsis

Tricarbonyliron complexes of α-methoxyheptadienone 3 and octadienone 8 were reacted as silyl enol ethers with protected β-hydroxypropanal and TiCl 4 , to give the syn-syn aldol condensation products 4 and 11 as major, isolated diastereomers (61 and 45%). Products 4 and 11 were converted into key intermediates of previous total syntheses of carbonolide B and tylonide, in a few steps, including the iron-directed reduction to syn diols and partial ozonolysis. The same methodology was used for the high yielding synthesis of a monofluorinated analog.