Stereochemical features of the [1,2]-Wittig rearrangement of O-glycosides derived from D-galactono- and D-xylono-γ-lactones: A new approach to the core part of zaragozic acids

✍ Scribed by Katsuhiko Tomooka; Makoto Kikuchi; Kazunobu Igawa; Ping-Huai Keong; Takeshi Nakai

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 247 KB
• Volume: 40
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(99)00043-x

✦ Synopsis

The Winig rearrangement of D-galactono-y-lactone derived [~O-glycoside is shown to al't~rd [5-C-glycoside (retention product), a potentially useful intermediate tbr zaragozic acid synthesis. By contrast, the rearrangement of the D-xylonolactone-derived counterpart was found to violate the retention principle to yield an inversion product as the major product.