Journal of Organic Chemistry p. 1177 - 1185 (1990)
Update date:2022-08-05
Topics:
Enhsen, Alfons
Karabelas, Kostas
Heerding, Julia M.
Moore, Harold W.
tert-Butoxyquinones were prepared from the thermal ring expansion of 4-alkynyl-, 4-alkenyl-, and 4-aryl-tert-butoxycyclobutenones and shown to be readily converted to hydroxyquinones upon treatment with trifluoroacetic acid at low temperature.This is a useful transformation since no reliable general route to hydroxyquinones has previously been available.The synthetic scope of this methodology as well as its specific utilization in the synthesis of a semisquaric acid, and the natural products, (+/-)-terreic acid, (+/-)-perezone, and (+/-)-isoperezone, are described.
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