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Total Synthesis of (−)-Acutumine

2009; American Chemical Society; Volume: 131; Issue: 19 Linguagem: Inglês

10.1021/ja9024403

1943-2984

L. Fang, Samuel S. Tartakoff, Steven L. Castle,

Alkaloids: synthesis and pharmacology

The first total synthesis of the tetracyclic alkaloid (−)-acutumine is described. Key reactions include an asymmetric ketone allylation mediated by Nakamura's chiral allylzinc reagent, an anionic oxy-Cope rearrangement, and the Lewis acid-promoted cyclization of an amine onto an α,β-unsaturated dimethyl ketal.