Totally Synthetic by Paul H. Docherty, 28 March 2006

Total Synthesis of Kendomycin

Smith

A. B. Smith, III, E. F. Mesaros, E. A. Meyer, J. Am. Chem. Soc. 2006, 128, 5292-5299.

DOI: 10.1021/ja060369+

Another synthesis by Amos Smith’s Group, this time of the macrolide Kendomycin, which they build up from four main fragments, resulting in a nicely convergent synthesis. As you might expect, the isolated double-bond is produced via a RCM step, completing the macrocycle. However, the olefin geometry was unfortunately inverse to the target, so an isomerisation was required. They tried to isomerise with iodine (always worth a go), but to no avail, as with the Vedejs and Oshima isomerisations, so they used technique similar to that previously used by McMurry, converting to an epoxide, and then reducing to the desired geometry.