Total Synthesis of Apoptolidin: Part 2. Coupling of Key Building Blocks and Completion of the Synthesis
No less than 30 stereogenic elements, a highly unsaturated 20‐membered macrocyclic system, four carbohydrate units, and unique biological activity, make the natural occurring apoptolidin (1) a challenging synthetic target. The retrosynthetic analysis revealed five key building blocks—three for the c...
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Veröffentlicht in: | Angewandte Chemie International Edition 2001-10, Vol.40 (20), p.3854-3857 |
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Hauptverfasser: | , , , , |
Format: | Artikel |
Sprache: | eng |
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Zusammenfassung: | No less than 30 stereogenic elements, a highly unsaturated 20‐membered macrocyclic system, four carbohydrate units, and unique biological activity, make the natural occurring apoptolidin (1) a challenging synthetic target. The retrosynthetic analysis revealed five key building blocks—three for the construction of the macrolide ring B and two prospective pendant saccharide units—which were synthesized in a highly convergent manner and then connected. Apoptolidin's rather labile nature proved particularly challenging in the final deprotection, purification, and characterization procedures. |
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ISSN: | 1433-7851 1521-3773 |
DOI: | 10.1002/1521-3773(20011015)40:20<3854::AID-ANIE3854>3.0.CO;2-D |