A Synthetic Approach to Nomofungin/Communesin B

A Synthetic Approach to Nomofungin/Communesin B

A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an ortho-quinone methide in...

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Veröffentlicht in:Organic letters 2003-09, Vol.5 (18), p.3169-3171
Hauptverfasser: Crawley, Seth L, Funk, Raymond L
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Cyclization
Epoxy Compounds - chemical synthesis
Indolequinones - chemistry
Molecular Structure
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Zusammenfassung:A highly stereoselective intramolecular cycloaddition of an indole tethered to an aza-ortho-xylylene intermediate effects the rapid construction of a substantial portion of the ring system of the cytotoxic natural product communesin B. An analogous cycloaddition involving an ortho-quinone methide intermediate provides an adduct that clearly revealed that the structural assignment for nomofungin was in error.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol034407v