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Total Synthesis of (±)-Communesin F

2007; American Chemical Society; Volume: 129; Issue: 45 Linguagem: Inglês

10.1021/ja075705g

1943-2984

Jun Yang, Haoxing Wu, Liqun Shen, Yong Qin,

Traditional and Medicinal Uses of Annonaceae

Total synthesis of the complex polycyclic indole alkaloid (±)-communesin F has been accomplished in 23 reaction steps in about 3% overall yield. The key steps relied on a highly efficient methodology for assembling the pentacyclic substructure 2 with the C7 quaternary carbon, the stereoselective preparation of the second C8 quaternary carbon by a two-step one-pot O-allylation and consecutive 3,3-rearrangement (2 to 3), and the stereoselective acid-catalyzed cyclization of 4 to form the azepine ring (5). These highly stereoselective reactions guaranteed the stereochemical results, allowing the construction of the C, E, F, and G ring systems.