Issue 21, 1994

Boron halide catalysed regioselective ortho-Claisen rearrangements of 4′-allyloxycoumaric acid derivatives: total synthesis of demethylsuberosin

Abstract

6-Allyl-7-hydroxycoumarin 3 and the naturally occurring linear coumarin, demethylsuberosin (7-hydroxy-6-prenylcoumarin)7 have been prepared in goods yields via regioselective boron halide catalysed ortho-Claisen rearrangements. This procedure provides an efficient alternative approach to linear substituted coumarins without using a halogen to block the 8-(angular) position.

Article information

Article type
Paper

J. Chem. Soc., Perkin Trans. 1, 1994, 3095-3100

Boron halide catalysed regioselective ortho-Claisen rearrangements of 4′-allyloxycoumaric acid derivatives: total synthesis of demethylsuberosin

N. Cairns, L. M. Harwood, D. P. Astles and A. Orr, J. Chem. Soc., Perkin Trans. 1, 1994, 3095 DOI: 10.1039/P19940003095

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