Importantly, this powerful and scalable transformation (conducted on decagram scale) proceeded with complete inversion of configuration to produce alkenyl furan 12, which contained the required (Z)-stereochemistry present in 1. After a straightforward methylation at C3 using n BuLi and methyl iodide (98% yield), the alkenyl silane served as a surrogate for an alkenylhalide via halodesilylation. Concerns that such a reaction would cause significant reversion of configuration of the alkene product back to (E) were unfounded as a satisfactory 5:1 ratio of easily separated products favoring (Z)-alkenyl bromide 13 resulted from treatment with NBS in acetonitrile (83% yield). The protocol listed above was used to prepare >15 grams of 13 thus far. The approach outlined above may be a generally useful strategy to procure highly substituted furans from furfural-based feedstocks.