Stereocontrolled synthesis of the C8-C22 fragment of rhizopodin |
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Authors: | Kretschmer Manuel Menche Dirk |
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Institution: | Universit?t Heidelberg, Institut für Organische Chemie, INF 270, D-69120 Heidelberg, Germany. |
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Abstract: | A convergent synthesis of the central C8-C22 core of the potent macrolide antibiotic rhizopodin is reported. Notable features of the stereocontrolled approach include an asymmetric reverse prenylation of an alcohol using a method of Krische, a thiazolium catalyzed transformation of an epoxyaldehyde as described by Bode, and a late-stage oxazole formation from advanced intermediates. This route demonstrates the applicability of these methodologies in complex natural product synthesis. |
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