Total synthesis of RK-397.
An enantioselective synthesis of the polyene macrolide RK-397 is described. The use of the same eight-carbon building block twice for the construction of the polyol chain allowed for a highly convergent synthesis. The synthesis highlights stereoselective vinylogous aldol addition using a chiral bisphosphoramide as well as a sequential palladium-catalyzed cross-coupling reaction for the preparation of key fragments.
Denmark
Scott E
SE
Department of Chemistry, University of Illinois at Urbana-Champaign, Urbana, Illinois 61801, USA. denmark@scs.uiuc.edu
Fujimori
Shinji
S
D018942:Macrolides / Q000138:chemical synthesis*; D008968:Molecular Conformation
D018942:Macrolides; C084367:RK 397