Lessons learned from macrolide synthesis |
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Authors: | Mulzer Johann Martin Harry J |
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Affiliation: | Institut für Organische Chemie der Universit?t Wien, W?hringer Strasse 38, A-1090 Wien, Austria. Johann.Mulzer@univie.ac.at |
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Abstract: | The highlights of three macrolide syntheses recently completed in our laboratory are described. In the epothilone B synthesis we developed the "early epoxide approach," which resulted in the first completely stereocontrolled synthesis of this natural product. In the laulimalide synthesis our contribution was the auxiliary controlled ene-macrocyclization and Sharpless' kinetic resolution for achieving a regioselective epoxidation of two pseudo-enantiomorphic allylic alcohol subunits. The tartrolon B synthesis was the first to be completed. In this case, a substrate controlled aldol addition was used to assemble the entire carbon skeleton of the compound. |
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Keywords: | antibiotics antitumor drugs aldol addition macrolactonization ene reaction Sharpless kinetic resolution |
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