Journal
TETRAHEDRON
Volume 57, Issue 26, Pages 5533-5542Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/S0040-4020(01)00479-3
Keywords
anodic oxidation; o-halogenated phenol; dihydrobenzopyran; rearrangement
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The spirodienones 5, 6, and 12-14 including optically active ones were synthesized by anodic oxidation of the corresponding phenol derivatives. Although the asymmetric centers included in the substrates had little effect on the diastereomeric selectivity of the cyclization, the asymmetric structure of the products led to a regioselective conversion into dihydrobenzopyrans 16, 17, and 21-26 under mild Lewis acid-promoted conditions. (C) 2001 Elsevier Science Ltd. All rights reserved.
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