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Diels-Alder reaction of furan with methyl 3-bromopropiolate: a route to methyl 3-oxo-7-oxabicyclo[2.2.1]hept-5-en-2-carboxylate

✍ Scribed by Jacques Leroy

Publisher: Elsevier Science
Year: 1992
Tongue: French
Weight: 301 KB
Volume: 33
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)79574-8

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✦ Synopsis

Abs&cC The two epimers of methyl 3-oxo-7-oxabicyclo[2.2.l]hept-S-en-2-carboxylate have been prepared from furan and methyl 3-bromopropiolate as a melhoxycarbonylketcne equivalent. The final step required hydrolysis of acetals by Nafion-H. 7-Oxabicyclo[2.2.l]hept-5-en-2-yl derivatives, in an optically active form, are powerful starting materials as chii templates ("naked sugars") for the synthesis of numerous natural compounds such as sugars, C-nucleosides, conduritols, etc.. 1 On the other hand, as a part of our studies directed toward the synthesis of 6-substituted analogues of shikimic acid via the base-promoted opening of bicylic esters,2 we

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