Asymmetric Total Synthesis of Batzelladine D

Asymmetric Total Synthesis of Batzelladine D

The first enantioselective total synthesis of a batzelladine alkaloid is described. The central reaction in the synthesis of (−)-batzelladine D (2) is a tethered Biginelli condensation of a guanidine aldehyde and an acetoacetic ester to generate a 7-substituted-1-iminohexahydropyrrolo[1,2-c]pyrimidi...

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Veröffentlicht in:Organic letters 1999-12, Vol.1 (13), p.2169-2172
Hauptverfasser: Cohen, Frederick, Overman, Larry E, Ly Sakata, Sylvie K
Format: Artikel
Sprache:eng
Schlagworte:
Alkaloids - chemical synthesis
Animals
Catalysis
Chromatography, High Pressure Liquid
Porifera - chemistry
Pyrimidines - chemical synthesis
Stereoisomerism
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Zusammenfassung:The first enantioselective total synthesis of a batzelladine alkaloid is described. The central reaction in the synthesis of (−)-batzelladine D (2) is a tethered Biginelli condensation of a guanidine aldehyde and an acetoacetic ester to generate a 7-substituted-1-iminohexahydropyrrolo[1,2-c]pyrimidine intermediate having the anti stereochemistry of the methine hydrogens flanking the pyrrolidine nitrogen.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol991269u