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Total Synthesis of the Antipode of Alkaloid 205 B

2003; Wiley; Volume: 42; Issue: 32 Linguagem: Inglês

10.1002/anie.200351906

1521-3773

Naoki Toyooka, Ayako Fukutome, Hiroyuki Shinoda, Hideo Nemoto,

Synthetic Organic Chemistry Methods

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.