Stereoselective synthesis of functionalized erythro/1,3-diols

✍ Scribed by Peter Mohr; Christoph Tamm

• Publisher: Elsevier Science
• Year: 1987
• Tongue: French
• Weight: 230 KB
• Volume: 28
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)95736-8

✦ Synopsis

v5+ -Catalyzed t-butylhydroperoxide epoxidation of (Z)-5-hydroxy-2- alkenylsilanes 4 exhibit good to excellent ervthro selectivity. The resulting epoxides undergo fragmentation to afford 1,3-diols 8, albeit in low chemical yield.

Many natural products of current interest contain either a 1,3-diol substructure like nonactic acid (1) or compactin (2) or even repeating 1,3-polyol groups like e.g. amphotericin, pimaricin, flavofungin or niphimycin. The 0