Tetracyclic monoterpene alkaloid alstilobanine A was obtained in racemic form. The pivotal steps of the total synthesis are a novel conjugate addition of an ester enolate with a nitrosoalkene, as well as a formal [2+2] intramolecular cycloaddition leading to a β-lactone to generate the requisite cis-fused 2-azadecalin moiety of the alkaloid. TMSE=trimethylsilylethoxy, Ts=4-toluenesulfonyl.
All Science Journal Classification (ASJC) codes
- General Chemistry