Preheat oven to 350°F (175°C). Grease and flour a 10-inch Bundt pan.
In a large bowl, whisk together flour, cocoa powder, baking powder, baking soda, and salt.
In a separate large bowl, combine granulated sugar, brown sugar, and vegetable oil. Mix until combined. Add buttermilk, eggs, and vanilla extract. Beat until smooth.
Gradually add dry ingredients to wet ingredients, mixing on low speed until just combined.
Carefully pour boiling water into the batter and mix until smooth. Stir in chopped semi-sweet chocolate.
Pour batter into prepared Bundt pan. Bake for 50-60 minutes, or until a wooden skewer inserted into the center comes out clean.
Let the cake cool in the pan for 10-15 minutes before inverting it onto a wire rack to cool completely.
While the cake is cooling, prepare the raspberry glaze. In a saucepan, heat raspberries over medium heat until they soften and release their juices.
Press raspberries through a fine-mesh sieve to remove seeds.
In a bowl, whisk together raspberry puree and powdered sugar. Add milk or water, one tablespoon at a time, until the glaze reaches desired consistency.
Once the cake is completely cool, drizzle raspberry glaze over the top. Let the glaze set for a few minutes before serving.