While Pd-catalyzed cyclopropane opening conditions only resulted in low conversion to the undesired enone side product (9-8) without any formation of the desired product (1-1), acid-catalyzed cyclopropane opening conditions, such as Amberlyst 15 led to partial decomposition of the starting material 9-7 (Scheme 9, Table ). Treatment of 9-7 with TsOH 61 gave the desired product (1-1) as a 1:1 mixture of C10 diastereomers in low yield. This result was attributed to the highly epimerizable a-position and the inability of the methyl ester containing substituent to control the facial selectivity of protonation. Zinc-mediated cyclopropanol opening conditions afforded enone (9-8) as the sole product in 16% yield, and radical opening conditions furnished a complex mixture of products (see Supporting Information Scheme SI3 for more details). Direct acid-catalyzed opening of the siloxycyclopro-panol was also attempted (not shown). However, xylogranatopyridine B (1-1) was formed as a minor product and a 1:1 mixture of diastereomers. Additional commonly employed cyclopropane opening conditions, such as HF•pyridine, NaOMe, and Pd/C-catalyzed hydrogenation all suffered from poor regioselectivity in this context.