Furan Oxidation Strategy for the Synthesis of the Macrolactone Analogue of Migrastatin.

Synthesis of the 14-membered macrolide core of migrastatin is accomplished by the use of furyl carbinol in 13 linear steps from furfural with ∼11% overall yield. Key strategies in the synthesis include the oxidative ring opening of furan and its use as a four-carbon synthon, SN2 displacement of a functionalized allyl bromide, and ring closing metathesis to obtain the macrolactone.