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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

2000; Royal Society of Chemistry; Issue: 24 Linguagem: Inglês

10.1039/b006623k

2050-8263

Kou Hiroya, Naoyuki Suzuki, Akito Yasuhara, Yuya Egawa, Atsushi Kasano, Takao Sakamoto,

Sirtuins and Resveratrol in Medicine

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.