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Novel strategies for the synthesis of anthrapyran antibiotics: discovery of a new antitumor agent and total synthesis of (S)-espicufolin

…, KM Gericke, RR Singidi, I Schuberth

文献索引:Tietze, Lutz F.; Gericke, Kersten M.; Singidi, Ramakrishna Reddy; Schuberth, Ingrid Organic and Biomolecular Chemistry, 2007 , vol. 5, # 8 p. 1191 - 1200

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被引用次数: 33

摘要

Two high-yielding strategies for the synthesis of 4H-anthra [1, 2-b] pyran antibiotics have been developed giving access to novel antitumor agent 24 (ED50 1.5 µM) and to (S)- espicufolin (3). A key step for the assembly of the tetracyclic 4H-anthra [1, 2-b] pyran-4, 7, 12- trione skeleton is the nucleophilic addition of an aryl lithium species onto an aldehyde which allows the introduction of either an ynone or 1, 3-diketo side chain, serving as precursors ...