Total Synthesis of the Antipode of Alkaloid 205 B

Total Synthesis of the Antipode of Alkaloid 205 B

Forming the tetrasubstituted piperidine ring with stereocontrol in a Michael‐type conjugate addition is a key step in the first enantioselective synthesis of the antipode 1 of alkaloid 205 B. The absolute stereochemistry of the natural product could be determined unambiguously by comparison of the o...

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Veröffentlicht in:Angewandte Chemie International Edition 2003-08, Vol.42 (32), p.3808-3810
Hauptverfasser: Toyooka, Naoki, Fukutome, Ayako, Shinoda, Hiroyuki, Nemoto, Hideo
Format: Artikel
Sprache:eng
Schlagworte:
alkaloids
Michael addition
natural products
nitrogen heterocycles
stereoelectronic effects
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Zusammenfassung:Forming the tetrasubstituted piperidine ring with stereocontrol in a Michael‐type conjugate addition is a key step in the first enantioselective synthesis of the antipode 1 of alkaloid 205 B. The absolute stereochemistry of the natural product could be determined unambiguously by comparison of the optical rotations.
ISSN:1433-7851
1521-3773
DOI:10.1002/anie.200351906