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Synfacts 2017; 13(10): 1007
DOI: 10.1055/s-0036-1591232
DOI: 10.1055/s-0036-1591232
Synthesis of Natural Products and Potential Drugs
Synthesis of (–)-Virosaine A
Weitere Informationen
Publikationsverlauf
Publikationsdatum:
18. September 2017 (online)
Significance
Virosaine A is a highly congested, polycyclic member of the Securinega alkaloid family. In their elegant synthetic approach towards (–)-virosaine A, Gleason and Hughes rely on an epoxide opening to trigger the intramolecular [3+2] cycloaddition proposed in its biosynthesis.
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Comment
Epoxide opening in oxabicycle F afforded nitrone G, which underwent an intramolecular cycloaddition reaction to give the pentacyclic core structure H. Subsequent alcohol protection and regioselective lithiation/bromination afforded intermediate I, which was converted to (–)-virosaine A by a sequence of five more transformations.
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