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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Vydáno v:	Journal of the American Chemical Society Ročník 131; číslo 10; s. 3472 - 3474
Hlavní autoři:	Martin, David B. C., Vanderwal, Christopher D.
Médium:	Journal Article
Jazyk:	angličtina
Vydáno:	WASHINGTON Amer Chemical Soc 18.03.2009
Témata:	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
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Popis
Shrnutí:	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.
Bibliografie:	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