Totally Synthetic by Paul H. Docherty, 13 January 2007
Total Synthesis of Merrilactone
W. He, J. Huang, X. Sun, A. J. Frontier, J. Am. Chem. Soc. 2007, 129, 498-499.
A great JACS article was posted at the close of last year by Alison Frontier at Rochester. Merrilactone has been a popular target, with syntheses by Danishefsky, Mehta and Inoue. Frontier’s approach was to use the incredibly interesting Nazarov Cyclisation to build the central C ring, and then use a radical cyclisation to complete the B ring. The implementation was sweet:
Although by no means convergent, this path allowed them to build up molecular complexity at an astonishing rate. Completion of the target took around nine steps, again in a linear fashion, and using more routine chemistry, but their judicious use of conditions allowed substrate directed additions and reductions, generating some useful distereomeric control.