Total Synthesis of the
Immunosupressant (-)-Pironetin
(PA48153C)
Gary E. Keck,*Chad E. Knutson, andSarah A. Wiles
Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020,
Salt Lake City, Utah 84112-0850
keck@chemistry.utah.edu
Received January 8, 2001
Abstract:
Total synthesis of the immunosuppresant pironetin has been achieved by a synthetic route in which the connections between starting materials
and the desired structure are readily discerned. Key steps include a diastereoselective Lewis acid mediated crotylstannane aldehyde addition,
a highly selective Lewis acid promoted Mukaiyama aldol reaction, an anti-selective SmI2 reduction of a -hydroxyketone, and finally a lactone
annulation reaction.
-hydroxyketone, and finally a lactone
annulation reaction.
