Step 1In a medium, heavy-bottom saucepan, combine the cherries with the sugar, brandy, wine, amaretto and orange liqueur. Scrape the seeds out of the vanilla bean into the pan, and combine with the other ingredients. Place the vanilla pod, cinnamon, peppercorns and orange zest in a small piece of cheesecloth and tie together to make a sachet (this will make it easier to discard once the cherries have been brandied). Place the sachet in the saucepan.
Step 2Bring the cherries to a boil over high heat, stirring frequently. Reduce the heat to a simmer and continue to cook for 10 minutes, stirring occasionally.
Step 3Strain the cherries from the liquid and set aside. Discard the sachet. Bring the liquid back to a simmer and continue to cook until it has thickened to a syrup and reduced to three-fourths cup, about 8 minutes. Remove from heat.
Step 4Combine the syrup with the cherries in a non-reactive container. This makes about 3 cups of brandied cherries. Cover and refrigerate until needed; the brandied cherries will keep, refrigerated, for months.
Step 1Heat the oven to 400 degrees. In a large bowl, sift together the flour, cocoa powder, sugar, baking powder and salt. Cut 5 tablespoons of the cold butter into half-inch pieces; incorporate the butter into the flour mixture using a pastry cutter or fork until crumbly. Stir in the chopped chocolate and brandied cherries.
Step 2In a medium bowl, whisk together the espresso and hot water until the espresso is dissolved. Stir in the heavy cream, sour cream and vanilla.
Step 3Stir the espresso mixture into the dough mixture. The mixture will still be very crumbly at first. Knead the dough (still in the bowl) with your hands until it just comes together. Lightly flour your work surface with cocoa powder and flatten the dough to 1 1/2 -inch thickness. Using a 2 1/2 -inch round biscuit cutter, cut the dough into 8 rounds. Place the rounds at least 2 inches apart on two stacked baking sheets lined with a sheet of parchment paper (the double layer of baking sheets will prevent the shortcakes from overcooking on the bottom before they are fully baked).
Step 4Melt the remaining 3 tablespoons butter. Lightly brush the top of each shortcake with melted butter. Lightly sprinkle the coarse sugar over the shortcakes and place in the oven. Bake the shortcakes until puffed and they spring back lightly when touched, 20 to 25 minutes, rotating the tray halfway through for even baking.
Step 5Remove the shortcakes, still on the parchment, to a rack. Cool completely. The shortcakes will keep for 3 days, covered, at room temperature.