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. Author manuscript; available in PMC: 2018 Jun 5.
Published in final edited form as: J Am Chem Soc. 2017 Sep 18;139(38):13562–13569. doi: 10.1021/jacs.7b07792

Scheme 1.

Scheme 1

Solvolytic epoxide opening cascade for the synthesis of a brominated pyrana

aReagents and conditions: (i) K2CO3 (1.5 equiv), 1,1,1,3,3,3-hexafluoroisopropanol (0.05 M), rt; (ii) HCl (concentrated aq., 5 equiv), wet Et2O, rt, 34% over two steps.