Total synthesis of the immunosupressant (-)-pironetin (PA48153C).
[reaction: see text]. 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 beta-hydroxyketone, and finally a lactone annulation reaction.
Keck
G E
GE
Department of Chemistry, University of Utah, 315 South 1400 East, RM 2020, Salt Lake City, Utah 84112-0850, USA. keck@chemistry.utah.edu
Knutson
C E
CE
Wiles
S A
SA
D007166:Immunosuppressive Agents / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D011753:Pyrones / Q000138:chemical synthesis*; D013302:Streptomyces / Q000737:chemistry
D007166:Immunosuppressive Agents; D007202:Indicators and Reagents; D011753:Pyrones; C088446:pironetin