Journal
TETRAHEDRON
Volume 66, Issue 27-28, Pages 5229-5234Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2010.04.075
Keywords
Spiroacetals; Spirocyclization; Ferrier rearrangement; Friedel-Crafts alkylation
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Funding
- National Science Council of Taiwan [NSC97-2113-M-039-001]
- China Medical University, Taiwan [CMU95-194, CMU97-226]
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A new spirocyclization was developed for the synthesis of 1,7-dioxaspiro[5.5]undecanes and 1-oxa-7-thiaspiro[5.5]undecanes by reaction of exo-glycal with aryl alcohols or thiophenols in the presence of Lewis acid BF(3)-OEt(2). The reaction proceeded through tandem Ferrier rearrangement, glycosylation, and Friedel Crafts alkylation to provide the corresponding products in good to excellent yields. Crown Copyright (C) 2010 Published by Elsevier Ltd. All rights reserved.
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