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
Hauptverfasser: Nicolaou, K. C., Li, Yiwei, Fylaktakidou, Konstantina C., Mitchell, Helen J., Sugita, Kazuyuki
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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.
ISSN:1433-7851
1521-3773
DOI:10.1002/1521-3773(20011015)40:20<3854::AID-ANIE3854>3.0.CO;2-D