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Solid-phase Synthesis of [4.4] Spirocyclic Oximes
Published on: February 6, 2019
Concise and stereoselective synthesis of the N7-C25 fragment of psymberin
Jason C Rech1, Paul E Floreancig
1Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Abstract:
[reaction: see text] The N7-C25 fragment of the potent and selective cytotoxic agent psymberin has been prepared through a short (12 linear steps, 15 total steps) and stereoselective sequence. Highlights of this route include a very rapid construction of the pentasubstituted arene, a substrate-controlled diastereoselective fragment coupling using a Mukaiyama aldol reaction, and an efficient entry into a key tetrahydropyranyl cyanide.
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