Organic letters

Stereospecific entry to [4.5] spiroketal glycosides using alkylidenecarbene CH insertion

DJ Wardrop, W Zhang, J Fritz

Index: Wardrop, Duncan J; Zhang, Wenming; Fritz, Joseph Organic letters, 2002 , vol. 4, # 4 p. 489 - 492

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Citation Number: 48

Abstract

A novel method for the stereospecific preparation of [4.5] spiroketal glycosides utilizing the 1, 5 CH bond insertion of alkylidenecarbenes is described. Treatment of 2-oxopropyl β- pyranosides A with lithium (trimethylsilyl) diazomethane in THF at-78° C afforded 1, 6- dioxaspiro [4, 5] decenes B in good yield. Submission of the corresponding α-glycosides C to the same reagent gave the isomeric insertion products D in moderate to high yield.

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