Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides

Alkaloid inspired spirocyclic oxindoles from 1,3-dipolar cycloaddition of pyridinium ylides

Cycloaddition reactions between pyridinium ylides and 3-alkenyl oxindoles that proceed in high yield and with very good regio- and diastereoselectivity are reported. The resulting cycloadducts have the same stereochemistry of biologically active oxindole alkaloids, such as strychnofoline.

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Veröffentlicht in:Organic & biomolecular chemistry 2013-10, Vol.11 (38), p.6502-6509
Hauptverfasser: Day, Jonathan, Uroos, Maliha, Castledine, Richard A, Lewis, William, McKeever-Abbas, Ben, Dowden, James
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemistry
Cyclization
Indoles - chemical synthesis
Indoles - chemistry
Molecular Structure
Pyridinium Compounds - chemistry
Spiro Compounds - chemical synthesis
Spiro Compounds - chemistry
Stereoisomerism
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Zusammenfassung:Cycloaddition reactions between pyridinium ylides and 3-alkenyl oxindoles that proceed in high yield and with very good regio- and diastereoselectivity are reported. The resulting cycloadducts have the same stereochemistry of biologically active oxindole alkaloids, such as strychnofoline.
ISSN:1477-0520
1477-0539
DOI:10.1039/c3ob41415a