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Issue 21, 1994
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Tandem thermal Claisen–Cope rearrangements of coumarate derivatives. Total syntheses of the naturally occurring coumarins: suberosin, demethylsuberosin, ostruthin, balsamiferone and gravelliferone

Abstract

Thermal Claisen rearrangements of derivatives of 4′-O-methyl and 4′-O-benzyl methyl coumarates 3, prepared from the corresponding umbelliferone derivatives, have been investigated. Simple allyl derivatives rearrange predominantly to the vacant ortho-position while prenyl derivatives undergo a sterically driven tandem para-Claisen rearrangement. After thermal rearrangement, the resulting 2′-hydroxycinnamate esters readily relactonise to yield 3-, 6- and 8-allylated coumarin derivatives in synthetically useful yields.

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Article type: Paper
DOI: 10.1039/P19940003101
J. Chem. Soc., Perkin Trans. 1, 1994, 3101-3107

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    Tandem thermal Claisen–Cope rearrangements of coumarate derivatives. Total syntheses of the naturally occurring coumarins: suberosin, demethylsuberosin, ostruthin, balsamiferone and gravelliferone

    N. Cairns, L. M. Harwood and D. P. Astles, J. Chem. Soc., Perkin Trans. 1, 1994, 3101
    DOI: 10.1039/P19940003101

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