Preheat oven to 350° F. Grease a bundt cake pan and coat with cocoa powder instead of flour.
Rinse and dry raspberries. Put in a small bowl with ¼ C sugar and gently stir to coat the raspberries in sugar. Set aside.
Combine red wine and sour cream in a cup, stir until sour cream is mixed into wine. Set aside.
In a medium sized bowl, sift flour and cocoa powder. I usually sift my cocoa powder with a sieve instead of my actual sifter. Add baking powder and salt and set aside.
In a microwave safe bowl, melt butter. Combine melted butter in mixing bowl with oil and sugar. Beat on medium speed for 3 minutes until light and fluffy.
Add eggs, one at a time, ensure that each egg is well beaten before adding the next one. After all eggs have been added, add the vanilla and chocolate extract. If you do not have chocolate extract, add 2 tablespoons of vanilla extract instead.
Alternate adding the flour mixture and the red wine mixture. First, pour in half of the dry ingredients and beat for 30 seconds before adding half of the red wine mixture. Repeat with remaining flour mixture and remaining red wine mix.
Gently fold in Raspberries. I save a handful of raspberries to also sprinkle around on top of my batter once it was poured in the pan.
Pour batter in the greased coated bundt cake pan. Bake at 350°F for 50-55 minutes. Check for doneness by inserting a toothpick into the center of the cake. If the toothpick comes out clean, your cake is done.
Transfer to a wire rack to cool for 30 minutes. After 30 minutes, place the wire rack on top of the bundt pan and flip it over. Gently tapping the sides to release the cake. You may want to put a piece of parchment paper or a plate over the cake before you flip it so you can easily move it off the wire rack without sticking. If the cake does not release, take a butter knife and gently insert along the edge of the pan to help release.
Once cake has cooled, prepare the glaze. Melt butter over medium heat in a sauce pan. Once butter is melted, add cocoa powder and heavy cream. Whisk together until mixture is thick and stir constantly for two minutes over heat to prevent from burning.
Remove from heat and add sifted confectionary sugar. Mixture will become very thick. Add vanilla extract and red wine and whisk until smooth.
If the glaze is too thin, return it to the heat for another 2-3 minutes until bubbling, stirring constantly. As the glaze cools, it will become a little thicker.
Drizzle glaze over cooled cake. I always put my cake on a wire rack overtop of a sheet pan. Once all the glaze has been poured, I remove the wire rack and gather up the extra glaze and pour over the cake again.