The 1-benzoxocane skeleton, present in the helianane natural products, presents a significant synthetic challenge. Intramolecular hydrosilylation of 2-methyl-5-heptyn-2-ol using Trost's conditions produces cyclic vinyl silane 1. Palladium-catalyzed coupling of 1 with aryl iodides proceeds in high yields to produce tertiary alcohols 2 that contain a Z-olefin. The presence of the olefin facilitates an intramolecular Buchwald-Hartwig etherification reaction to produce the 1-benzoxocane skeleton 3. Hydrogenation of the olefin produced helianane. Effects of different R groups, bases, and ligands on the cyclization will be presented.