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Stereoselective Synthesis of (+)-Aspidofractinine
The Journal of Organic Chemistry2009Vol. 74(16), pp. 6035–6041
Citations Over TimeTop 13% of 2009 papers
Abstract
We describe the synthesis of (+)-aspidofractinine, the enantiomer of a naturally occurring alkaloid of the kopsane family. Key features of the synthesis include a stereospecific cyanate to isocyanate rearrangement on a chiral scaffold, a ring-closing alkene metathesis to cleave the chiral auxiliary, and a chemoselective cyclopropanation to introduce the quaternary carbon at position 7 of aspidofractinine.
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