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Synfacts 2008(12): 1259-1259
DOI: 10.1055/s-0028-1083612
DOI: 10.1055/s-0028-1083612
Synthesis of Heterocycles
© Georg Thieme Verlag
Stuttgart ˙ New York
A Diels-Alder Approach to Benzannulated [5,6]-Spiroketals
C. D. Bray*
University of London, UK
Further Information
Publication History
Publication Date:
20 November 2008 (online)

Significance
Reported is the synthesis of arylsubstituted benzannulated [5,6]-spiroketals from the thermal reaction of 2-hydroxybenzylacetates with γ-methylene-γ-butyrolactone. The reaction proceeds via an ortho-quinone methide which then undergoes Diels-Alder cycloaddition to give the spiroketal products. The starting acetates were synthesized in high yield through selective acetylation of the requisite 2-hydroxybenzyl alcohols.