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Drain tomatoes in fine-mesh strainer over large bowl. Open tomatoes and remove and discard seeds and fibrous cores. Let tomatoes drain
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Heat 2 Tbsp oil in skillet over medium heat. Add onion and cook until softened and lightly browned (~5 min)
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Stir in garlic and oregano and cook until fragrant
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Stir in all but 3/4 cup of drained tomatoes and increase heat to med-high. Cook, stirring often, until liquid has evaporated and tomatoes begin to brown and stick to pan (~10-12 min)
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Stir in wine and cook until thick and syrupy (~1 min). Stir in collected tomato juice and simmer until sauce has thickened (~10 min)
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Add reserved 3/4 cup tomatoes and process/blend until slightly chunky (~8 pulses). Return sauce to skillet and stir in basil and 1 Tbsp oil
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Season with salt, pepper, and sugar to taste
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Can add some pasta cooking water if serving with pasta