Access to epoxide 24 allowed us to examine the proposed House-Meinwald rearrangement to finish the A-ring sterotriad. As illustrated in Scheme 6, this approach ultimately proved to be intractable. We surveyed an exhaustive series of Lewis acids under varying conditions. These included Brønstead acids as well as various boron, aluminum, scandium, indium, rhenium, and iridium reagents. The desired rearrangement product was not observed under any condition. Instead, the most consistent product from these reactions was ketone 25. This species was produced alongside variable quantities of structures 26-28 and several other uninterpretable products. These results are likely explained by a mechanism involving carbocation A as shown in Scheme 6. The main reaction pathway involves fragmentation of the C2-C3 s-bond to provide B. A retro-aldol reaction then produces 25. Several secondary pathways were also observed. Thus, epoxide 26 arises from a [1,2]-shift of the C2 hydrogen in A and capture of the resultant carbocation by the pendant C3 alcohol. Conversely, ketone 27 is a decomposition product from [1,2]-rearrangement of the epoxide, subsequent dehydration of the C3 alcohol, and further isomerization of the resultant alkene. As evidence by alkene 28, dehydration at C3 is also possible. This complex reactivity profile suggests that ionization of the C6-O s-bond in allylic epoxide 24 impedes practical access to the A-ring stereotriad from 24. Alternative strategies to reduce epoxide 24 (e.g. BF3•OEt3, NaBH4) 34 or oxidize the A-ring alkene in 23 (e.g. HBR2; H2O2, NaOH) were complicated by poor regio-and chemoselectivity. Collectively, these outcomes call for a revised approach to the A-ring of 1.