Total Synthesis of Apoptolidin: Part 1. Retrosynthetic Analysis and Construction of Building Blocks
- 15 October 2001
- journal article
- research article
- Published by Wiley in Angewandte Chemie International Edition in English
- Vol. 40 (20) , 3849-3854
- https://doi.org/10.1002/1521-3773(20011015)40:20<3849::aid-anie3849>3.0.co;2-m
Abstract
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.This publication has 35 references indexed in Scilit:
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