Concise means for accessing an advanced precursor to 1-deoxypaclitaxel.
A program directed toward a total synthesis of 1-deoxypaclitaxel is described. The most direct route consists of six steps from the previously described diketone 12 and proceeds in 18% overall yield. The transformations involved in reaching the target molecule 22 consist of stereoselective alpha-ketol generation, an EtAlCl(2)-catalyzed transannular hydride shift, regioselective monomesylation, and a Wagner-Meerwein 1,2-shift. The central issue of this synthesis is the sequential deployment of these highly controlled steps along the perimeter and across the interior gap of a nine-membered ring.
Guo
Xin
X
Evans Chemical Laboratories, The Ohio State University, Columbus, Ohio 43210, USA.
Paquette
Leo A
LA
D020650:Combinatorial Chemistry Techniques; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D017239:Paclitaxel / Q000031:analogs & derivatives* / Q000032:analysis / Q000138:chemical synthesis*; D013237:Stereoisomerism
C496493:1-deoxypaclitaxel; D007202:Indicators and Reagents; D017239:Paclitaxel