Organic Chemistry Portal
Reactions >> Total Syntheses

Totally Synthetic by Paul H. Docherty, 21 April 2006

Total Synthesis of 6-Deoxyerythronolide B


M. T. Crimmins, D. J. Slade, Org. Lett. 2006, 8, 2194-2194

DOI: 10.1021/ol0607241

Formal total synthesis of 6-Deoxyerythronolide B, using Crimmins aldol methodology to install eight of the nine stereocenters. Their method revolves around the iterative asymmetric acyl-thiazolidinethione propionate aldol reaction:

Getting around 80% yield and >20:1 dr in each of these aldol reactions makes this a pretty sweet job, if a little repetitive.