Issue 4, 1993

Synthesis of 5-hydroxy-1,7-dioxaspiro[5.5]undec-3-en-2-ones from 2-benzenesulfonyltetrahydropyrans and 5-hydroxybutenolides: X-ray crystal structure determination for (5RS,6SR)-5-acetoxy-4-methoxy3-methyl-1,7-dioxaspiro[5.5]undec-3-en-2-one

Abstract

5-Hydroxy-1,7-dioxaspiro[5.5]undec-3-en-2-ones are obtained from reactions between 2-lithiated 2-benzenesulfonyltetrahydropyrans and 5-hydroxybutenolides. The structure of (5RS,6SR)-5-acetoxy-4methoxy-3-methyl-1,7-dioxaspiro[5.5]undec-3-en-2-one 16 was confirmed by X-ray crystallography. Addition of 5-lithiated 2,3-dihydrofuran and 6-lithiated 3,4-dihydro-2H-pyran to the hydroxybutenolide 12 gave the butenolides 30 and 31. Hydrolysis of 31 gave 33, which on dehydration returned 31 rather the conjugated isomer 32.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1993, 411-416

Synthesis of 5-hydroxy-1,7-dioxaspiro[5.5]undec-3-en-2-ones from 2-benzenesulfonyltetrahydropyrans and 5-hydroxybutenolides: X-ray crystal structure determination for (5RS,6SR)-5-acetoxy-4-methoxy3-methyl-1,7-dioxaspiro[5.5]undec-3-en-2-one

A. M. Baylis, M. Helliwell, A. C. Regan and E. J. Thomas, J. Chem. Soc., Perkin Trans. 1, 1993, 411 DOI: 10.1039/P19930000411

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