Total Syntheses of (−)-Haemanthidine, (+)-Pretazettine, and (+)-Tazettine

Autor: Baldwin, S. W., Debenham, J. S.
Zdroj: Organic Letters; January 2000, Vol. 2 Issue: 2 p99-102, 4p
Abstrakt: The total syntheses of the amaryllidaceae alkaloids haemanthidine, pretazettine, and tazettine as optically pure enantiomers are reported. Using d-mannose as the starting material, the critical relative stereochemical relationships are established with an intramolecular nitrone−alkene cycloaddition reaction. The synthetic route leads successively to (−)-haemanthidine and then to (+)-pretazettine and (+)-tazettine, taking advantage of the well-established complex relationships among these three alkaloids.
Databáze: Supplemental Index