Stereocontrolled synthesis of the C8-C22 fragment of rhizopodin
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...
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| Main Authors: | , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2012
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| In: |
Organic letters
Year: 2011, Volume: 14, Issue: 1, Pages: 382-385 |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/ol203130b |
| Online Access: | Verlag, kostenfrei registrierungspflichtig, Volltext: http://doi.org/10.1021/ol203130b Verlag, kostenfrei registrierungspflichtig, Volltext: https://pubs.acs.org/doi/abs/10.1021/ol203130b 
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| Author Notes: | Manuel Kretschmer, Dirk Menche |
| Summary: | 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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| Item Description: | Published online: December 13, 2011 Gesehen am 26.04.2018 |
| Physical Description: | Online Resource |
| ISSN: | 1523-7052 |
| DOI: | 10.1021/ol203130b |