Total Synthesis of Spirastrellolide F Methyl Ester—Part 1: Strategic Considerations and Revised Approach to the Southern Hemisphere

Abstract

In readiness for closure: To ensure optimal convergence in the projected total synthesis of spirastrellolide F, the building block representing the southern hemisphere was prepared with a free carboxylic acid and an enol triflate (Tf) terminus (see picture). This unusual pattern allows the 38-membered macrocyclic core of this potent antimitotic agent to be constructed, while keeping late-stage protecting-group manipulations to a minimum.