Nikolaos Papaioannou, Jarred T. Blank, Scott J. Miller
Feb 25, 2003
Citations
0
Influential Citations
28
Citations
Journal
The Journal of organic chemistry
Abstract
An enantioselective synthesis of mitosane core (-)-1 has been achieved. Key steps include a rapid assembly of a key eight-membered-ring intermediate employing ring-closing metathesis. Kinetic resolution of an advanced secondary alcohol was then accomplished by using a peptide-based asymmetric acyl transfer catalyst that was discovered from a parallel screen of catalyst candidates. Optically pure material was then converted to the mitosane core, which was the subject of additional studies on the selective modification to produce several substituted compounds containing a mitosane ring system.