Triflic acid-mediated rearrangements of 3-methoxy-8-oxabicyclo [3.2. 1] octa-3, 6-dien-2-ones: synthesis of methoxytropolones and furans

YD Williams, C Meck, N Mohd…

Index: Williams, Yvonne D.; Meck, Christine; Mohd, Noushad; Murelli, Ryan P. Journal of Organic Chemistry, 2013 , vol. 78, # 23 p. 11707 - 11713

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Citation Number: 15

Abstract

Methoxytropolones are useful scaffolds for therapeutic development because of their known biological activity and established value in the synthesis of α-hydroxytropolones. Upon treatment with triflic acid, a series of 3-methoxy-8-oxabicyclo [3.2. 1] octa-3, 6-dien-2-ones rearrange rapidly and cleanly to form methoxytropolones. Interestingly, bicycles that are derived from dimethyl acetylenedicarboxylate (R2= R3= CO2Me) instead form furans as ...