Novel strategies for the synthesis of anthrapyran antibiotics: discovery of a new antitumor agent and total synthesis of (S)-espicufolin |
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Authors: | Tietze Lutz F Gericke Kersten M Singidi Ramakrishna Reddy Schuberth Ingrid |
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Institution: | Institut für Organische und Biomolekulare Chemie, Georg-August-Universit?t, Tammannstrasse 2, 37077, G?ttingen, Germany. ltietze@gwdg.de |
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Abstract: | Two high-yielding strategies for the synthesis of 4H-anthra1,2-b]pyran antibiotics have been developed giving access to novel antitumor agent (ED(50) 1.5 microm) and to (S)-espicufolin (3). A key step for the assembly of the tetracyclic 4H-anthra1,2-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 for an acid-catalysed cyclisation. |
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