Totally Synthetic by Paul H. Docherty, 26 April 2006

Total Synthesis of Mucocin

Crimmins

M. T. Crimmins, Y. Zhang, F. A. Diaz, Org. Lett. 2006, 8, 2369-2372.

DOI: 10.1021/ol060704z

Ruthenium-tastic total synthesis of the polyether Mucocin, using three metathesis reactions in this paper. Most interesting was the creation of the central THF as a 2,5-DHF via a Hoye-type activation strategy. This involves using a allyloxymethyl side chain to direct the Ru complex insertion, resulting in preferential formation of the 5-member ring.

Coupling of this fragment to the right-hand piece proceeded via a efficient Sonogashira coupling and subsequent diimide reduction, whilst the left-hand section was inserted via metathesis, in a similar fashion to Mootoo’s synthesis.