Efficient Access to the Core of the Strychnos, Aspidosperma and Iboga Alkaloids. A Short Synthesis of Norfluorocurarine

An efficient anionic bicyclization of tryptamine-derived Zincke aldehydes forms the basis for a three-step route to the tetracyclic ABCE core of many Strychnos, Aspidosperma, and Iboga alkaloids. This powerful reaction is showcased in a five-step synthesis of the Strychnos alkaloid norfluorocurarine...

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Veröffentlicht in:Journal of the American Chemical Society Jg. 131; H. 10; S. 3472 - 3474
Hauptverfasser: Martin, David B. C., Vanderwal, Christopher D.
Format: Journal Article
Sprache:Englisch
Veröffentlicht: WASHINGTON Amer Chemical Soc 18.03.2009
Schlagworte:
Alkaloids - chemistry
Aspidosperma - chemistry
Chemistry
Chemistry, Multidisciplinary
Crystallography, X-Ray
Physical Sciences
Science & Technology
Strychnos - chemistry
Tabernaemontana - chemistry
Tubocurarine - analogs & derivatives
Tubocurarine - chemical synthesis
REARRANGEMENT
GLUTACONALDEHYDE
ENTRY
PRODUCTS
PHENYL-PYRIDINIUM CHLORIDE
MIDDLE CORE
CASCADE
DERIVATIVES
STEREOCONTROLLED SYNTHESIS
POLYCYCLIZATION
ISSN:0002-7863, 1520-5126, 1520-5126
Online-Zugang:Weitere Angaben
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Beschreibung
Zusammenfassung:An efficient anionic bicyclization of tryptamine-derived Zincke aldehydes forms the basis for a three-step route to the tetracyclic ABCE core of many Strychnos, Aspidosperma, and Iboga alkaloids. This powerful reaction is showcased in a five-step synthesis of the Strychnos alkaloid norfluorocurarine from tryptamine and pyridine.
Bibliographie:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0002-7863
1520-5126
1520-5126
DOI:10.1021/ja900640v