Total Synthesis and Structural Revision of Sekothrixide

Total Synthesis and Structural Revision of Sekothrixide

The first total synthesis of 14-membered macrolide sekothrixide and the originally proposed structure are reported. Seven contiguous asymmetric centers in the side chain were constructed using ring-openings of several kinds of epoxide. Assembly of the left segment and right segment was performed on...

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Veröffentlicht in:Organic letters 2014-06, Vol.16 (11), p.2794-2797
Hauptverfasser: Terayama, Naoki, Yasui, Eiko, Mizukami, Megumi, Miyashita, Masaaki, Nagumo, Shinji
Format: Artikel
Sprache:eng
Schlagworte:
Heterocyclic Compounds - chemical synthesis
Heterocyclic Compounds - chemistry
Lactones - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:The first total synthesis of 14-membered macrolide sekothrixide and the originally proposed structure are reported. Seven contiguous asymmetric centers in the side chain were constructed using ring-openings of several kinds of epoxide. Assembly of the left segment and right segment was performed on the basis of the RCM reaction to generate 14-membered lactones having an E-trisubstituted olefin. These synthetic results led to a revision of C4, C6, and C8 stereochemistry in the structure of natural sekothrixide.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol5006856