期刊
JOURNAL OF ORGANIC CHEMISTRY
卷 74, 期 21, 页码 8480-8483出版社
AMER CHEMICAL SOC
DOI: 10.1021/jo901855p
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资金
- Natural Sciences and Engineering Research Council of Canada (NSERC)
- FQRNT (Quebec)
Selective syntheses of methyl alpha- (8) and beta-C-mannopyranosyl acrylates (9) were obtained from alpha-C-allyl mannopyranoside (3) by ozonolysis to 4 followed by alpha-methylenation to provide intermediate aldehydes 5 and 6. The beta-anomer 6 was obtained by in situ anomeric epimerization. The acrylates and the homologous alpha-anomer 16, obtained by oxidative hydroboration, oxidation, and alpha-methylenation, were converted into 3-C-linked mannopyranosyl coumarins 11, 12,and 19 in good yields under one-pot Heck/lactonization conditions.
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