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A Unified Strategy for the Synthesis of Phenanthroizidine Alkaloids: Preparation of Sterically Congested Pyridines

1996; American Chemical Society; Volume: 118; Issue: 48 Linguagem: Inglês

10.1021/ja962757p

1943-2984

Marco A. Ciufolini, Frank Roschangar,

Traditional and Medicinal Uses of Annonaceae

Total syntheses of the representative phenanthroizidine alkaloids, tylophorine and antofine, and of their seco congeners, septicine and julandine, have been completed from sterically congested 3,4-diarylpyridines prepared by a modified Knoevenagel−Stobbe synthesis. Central to the success of this effort was the ability of α-dicarbonyl enones to combine in a formal [4 + 2]-cycloaddition with sterically demanding vinyl ethers.