In practice, this transformation proved to be very challenging to achieve. The desired syn-1,2 stereochemistry present in 1 necessitated either double inversion at C7, or a diastereoselective SN1 reaction. Unfortunately, a series of established epoxide-opening transformations resulted in no reactivity or poor diastereoselectivity (see Supporting Information for details). During these investigations, we noted that vinyl epoxide 10 was prone to ionization and rearrangement under a variety of relatively mild conditions, so we sought to exploit this to perform an SN1 reaction in the absence of a strong Lewis or Brønsted acid. Heating the epoxide and alcohol neat on silica gel or acidic alumina provided desired ether 21 in low yield along with the C6 ketone resulting from a Meinwald rearrangement. To ameliorate this problem, we elected to heat alcohol 9 and epoxide 10 together in the absence of acidic additives or solvent. This successfully delivered the desired ether 21 as the major product, albeit in low yield. Unfortunately, the elevated temperatures required for this reaction led to spontaneous decomposition. We reasoned that the sensitive allylic positions on 9 and 10 could be easily ionized, even by the slightly acidic glassware surface. While silanization failed to provide reproducible results, performing the reaction in plastic vessels afforded the desired ether 21 in 65% yield and as a single diastereomer.