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

Publication ,  Journal Article
Baldwin, SW; Debenham, JS
Published in: Organic letters
January 2000

[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.

Duke Scholars

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

January 2000

Volume

2

Issue

2

Start / End Page

99 / 102

Related Subject Headings

  • Stereoisomerism
  • Plant Extracts
  • Phenanthridines
  • Organic Chemistry
  • Antineoplastic Agents, Phytogenic
  • Amaryllidaceae Alkaloids
  • Alkaloids
  • 34 Chemical sciences
  • 03 Chemical Sciences
 

Citation

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Baldwin, S. W., & Debenham, J. S. (2000). Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine. Organic Letters, 2(2), 99–102. https://doi.org/10.1021/ol9911472
Baldwin, S. W., and J. S. Debenham. “Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine.Organic Letters 2, no. 2 (January 2000): 99–102. https://doi.org/10.1021/ol9911472.
Baldwin SW, Debenham JS. Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine. Organic letters. 2000 Jan;2(2):99–102.
Baldwin, S. W., and J. S. Debenham. “Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine.Organic Letters, vol. 2, no. 2, Jan. 2000, pp. 99–102. Epmc, doi:10.1021/ol9911472.
Baldwin SW, Debenham JS. Total syntheses of (-)-haemanthidine, (+)-pretazettine, and (+)-tazettine. Organic letters. 2000 Jan;2(2):99–102.
Journal cover image

Published In

Organic letters

DOI

EISSN

1523-7052

ISSN

1523-7060

Publication Date

January 2000

Volume

2

Issue

2

Start / End Page

99 / 102

Related Subject Headings

  • Stereoisomerism
  • Plant Extracts
  • Phenanthridines
  • Organic Chemistry
  • Antineoplastic Agents, Phytogenic
  • Amaryllidaceae Alkaloids
  • Alkaloids
  • 34 Chemical sciences
  • 03 Chemical Sciences