On Robert B. Woodward and the Total Synthesis of Quinine

EDMUNDO A. RÚVEDA; TEODORO S. KAUFMAN

THE CHEMICAL EDUCATOR

Springer

Lugar: Nueva York; Año: 2004 vol. 9 p. 172 - 176

1430-4171

In 1944, Woodward and Doering succeeded in converting 8-hydroxyisoquinoline into (±)-homomeroquinene, a protected form of which was transformed into (±)-quinotoxine, which was optically resolved, yielding d-quinotoxine. Quinotoxine is a degradation product of quinine, known since the middle of the 19th century, which Rabe reported to have converted into quinine, in 1918. This constituted the first modern and complex rational approach to quinine and a formal total synthesis of the natural product. Since Woodward?s publication, several total syntheses of quinine were disclosed, by Uskokovic (1970-1978), Stork (2001), Jacobsen (2004) and Kobayashi (2004), displaying each new one increasing degrees of stereocontrol and atom economy.