Concise and stereoselective synthesis of the N7-C25 fragment of psymberin.
[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.
Rech
Jason C
JC
Department of Chemistry, University of Pittsburgh, Pittsburgh, Pennsylvania 15260, USA.
Floreancig
Paul E
PE
D002384:Catalysis; D003374:Coumarins; D003486:Cyanides / Q000737:chemistry; D003603:Cytotoxins / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D011714:Pyrans / Q000138:chemical synthesis* / Q000737:chemistry; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003374:Coumarins; D003486:Cyanides; D003603:Cytotoxins; D011714:Pyrans; D011753:Pyrones; C498383:psymberin