期刊
ORGANIC LETTERS
卷 4, 期 4, 页码 489-492出版社
AMER CHEMICAL SOC
DOI: 10.1021/ol016975l
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资金
- NIGMS NIH HHS [GM59157-01] Funding Source: Medline
A novel method for the stereospecific preparation of [4.5]spiroketal glycosides utilizing the 1,5 C-H bond insertion of alkylidenecarbenes is described. Treatment of 2-oxopropyl beta-pyranosides A with lithium (trimethylsilyl)diazomethane in THF at -78 degreesC afforded 1,6-dioxaspiro[4,5]decenes B in good yield. Submission of the corresponding a-glycosides C to the same reagent gave the isomeric insertion products D in moderate to high yield.
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