Fluorous Mixture Synthesis of (−)-Dictyostatin and Three Stereoisomers

Fluorous Mixture Synthesis of (−)-Dictyostatin and Three Stereoisomers

A mixture of four stereoisomers whose configurations are encoded by fluorous silyl protecting groups has been prepared and converted over 22 steps to a mixture of protected dictyostatins. Demixing by fluorous HPLC followed by removal of the fluorous protecting groups (detagging) provides dictyostati...

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Veröffentlicht in:Organic letters 2006-01, Vol.8 (2), p.301-304
Hauptverfasser: Fukui, Yoshikazu, Brückner, Arndt M, Shin, Youseung, Balachandran, Raghavan, Day, Billy W, Curran, Dennis P
Format: Artikel
Sprache:eng
Schlagworte:
Fluorine - chemistry
Macrolides - chemical synthesis
Macrolides - chemistry
Molecular Structure
Stereoisomerism
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Zusammenfassung:A mixture of four stereoisomers whose configurations are encoded by fluorous silyl protecting groups has been prepared and converted over 22 steps to a mixture of protected dictyostatins. Demixing by fluorous HPLC followed by removal of the fluorous protecting groups (detagging) provides dictyostatin and three C6,C7 stereoisomers. Biological evaluation showed that the monoepimers of the natural product retained highly potent activity.
ISSN:1523-7060
1523-7052
DOI:10.1021/ol0526827