In a small saucepan, combine 1/4 cup of the sugar and the wine, and dissolve, stirring, over medium-low heat, and slightly reduced, about 2 minutes. Remove from the heat and cool. Combine the raspberries and syrup in a bowl and toss gently to combine.
In a bowl whip the heavy cream until it is nearly doubled in volume. Add the remaining 2 tablespoons sugar and whip until it forms stiff peaks.
Spread 1 tablespoon of chocolate on the bottom of a dessert plate, and top with 1 pear slice. Layer with 1 tablespoon of cream, raspberries, 1 teaspoon of chocolate, and 1 pear slice, and repeat to make 6 layers in all, finishing with raspberries and chocolate on top. Repeat with the remaining ingredients, to make 4 napoleons in all.
Yield: 4 servings