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

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• 作者：Marco A. Ciufolini and Frank Roschangar
• 刊名：Journal of the American Chemical Society
• 出版年：1996
• 出版时间：December 4, 1996
• 年：1996
• 卷：118
• 期：48
• 页码：12082 - 12089
• 全文大小：455K
• 年卷期：v.118,no.48(December 4, 1996)
• ISSN：1520-5126

文摘

Total syntheses of the representative phenanthroizidine alkaloids,tylophorine and antofine, and of theirseco congeners, septicine and julandine, have been completed fromsterically congested 3,4-diarylpyridines preparedby a modified Knoevenagel-Stobbe synthesis. Central to thesuccess of this effort was the ability of -dicarbonylenones to combine in a formal [4 + 2]-cycloaddition with stericallydemanding vinyl ethers.