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Rustic Plum and Port Tart

['2 cups tawny Port', '1/2 cup (packed) plus 1 tablespoon golden brown sugar', '1/4 teaspoon allspice', '1 1/2 pounds plums (5 to 6 medium), halved, pitted, each half quartered', '1 tablespoon all purpose flour', '1 refrigerated pie crust (half of 15-ounce package)', 'Vanilla ice cream']

Preheat oven to 375°F. Boil Port, 1/2 cup brown sugar, and allspice in large skillet until reduced to 2/3 cup, about 10 minutes. Place plums in large bowl. Sprinkle flour over; toss to coat. Drizzle 1/3 cup syrup over plums; toss to coat. Reserve remaining syrup.
Unroll cold pie crust onto parchment-lined baking sheet. Spoon plums into center of crust, leaving 1 1/2-inch border; drizzle any remaining syrup from bowl over plums. Fold crust edges over plums. Brush crust with water; sprinkle crust and plums with remaining 1 tablespoon brown sugar.
Bake tart until crust is golden and syrup is bubbling, about 45 minutes. Cut warm or room-temperature tart into wedges. Serve with scoop of vanilla ice cream, drizzling additional syrup over.

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