Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine.

Journal Article (Journal Article)

[structures: see text] 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.

Full Text

Duke Authors

Cited Authors

  • Baldwin, SW; Debenham, JS

Published Date

  • January 2000

Published In

Volume / Issue

  • 2 / 2

Start / End Page

  • 99 - 102

PubMed ID

  • 10814256

Electronic International Standard Serial Number (EISSN)

  • 1523-7052

International Standard Serial Number (ISSN)

  • 1523-7060

Digital Object Identifier (DOI)

  • 10.1021/ol9911472


  • eng