Subscribe to RSS
Please copy the URL and add it into your RSS Feed Reader.
https://www.thieme-connect.de/rss/thieme/en/10.1055-s-00000131.xml
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
Further Information
Publication History
Publication Date:
18 September 2017 (online)
![](https://www.thieme-connect.de/media/synfacts/201710/i_c050_s1_10-1055_s-0036-1591232.gif)
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.
#
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.
#
#
![](https://www.thieme-connect.de/media/synfacts/201710/i_c050_s1_10-1055_s-0036-1591232.gif)