Synthesis of natural polyacetylenes bearing furan rings.
The first total syntheses of four new polyacetylene compounds have been achieved using convergent routes, which involved Cadiot--Chodkiewicz copper-catalyzed cross-coupling reactions to sp-sp centers as the key steps. 19-Furan-2-ylnonadeca-5,7-diynoic acid (1), 19-furan-2-ylnonadeca-5,7-diynoic acid methyl ester (2), 2-pentacosa-7,9-diynylfuran (3), and 21-furan-2-ylhenicosa-14,16-diyn-1-ol (4) were stable and could be readily identified, isolated, and purified in high overall yields.
Barancelli
Daniela A
DA
Laboratório de Sintese, Reatividade, Avaliação, Toxicologica e Farmacologica de Organocalcogenios-CCNE-UFSM, 97105-900-Santa Maria, RS, Brazil.
Mantovani
Anderson C
AC
Jesse
Cristiano
C
Nogueira
Cristina W
CW
Zeni
Gilson
G
D001688:Biological Products / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D005663:Furans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D053279:Polyynes / Q000138:chemical synthesis* / Q000737:chemistry
D001688:Biological Products; D005663:Furans; D053279:Polyynes; D003300:Copper; C039281:furan