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
APA
Chicago
ICMJE
MLA
NLM
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.
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