Issue 24, 2000

Total syntheses of three natural products, vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol from a common starting material

Abstract

Vignafuran 2, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester 3, and coumestrol 4 were efficiently synthesized from the same starting material, 4-bromoresorcinol 14a, through the common intermediate, diarylacetylene 7. The key steps of these syntheses were the tetrabutylammonium fluoride (TBAF )-catalyzed benzo[b]furan ring formation for 2 and the carbonylative ring closure methodology catalyzed by a Pd complex for 3 and 4.

Article information

Article type
Paper
Submitted
14 Aug 2000
Accepted
29 Sep 2000
First published
20 Nov 2000

J. Chem. Soc., Perkin Trans. 1, 2000, 4339-4346

Total syntheses of three natural products, vignafuran, 2-(4-hydroxy-2-methoxyphenyl)-6-methoxybenzofuran-3-carboxylic acid methyl ester, and coumestrol from a common starting material

K. Hiroya, N. Suzuki, A. Yasuhara, Y. Egawa, A. Kasano and T. Sakamoto, J. Chem. Soc., Perkin Trans. 1, 2000, 4339 DOI: 10.1039/B006623K

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