Step 1

Pour tomatoes and juice into strainer set over large bowl. Open tomatoes with hands and remove and discard fibrous cores; let tomatoes drain excess liquid, about 5 minutes. Remove 3/4 cup tomatoes from strainer and set aside. Reserve 2 1/2 cups tomato juice and discard remainder.

Step 2

Heat olive oil in large skillet over medium heat until shimmering. Add onion and cook, stirring occasionally, until softened and golden around edges, 6 to 8 minutes. Add garlic and oregano and cook, stirring constantly, until garlic is fragrant, about 30 seconds.

Step 3

Add tomatoes from strainer and increase heat to medium-high. Cook, stirring every minute, until liquid has evaporated and tomatoes begin to stick to bottom of pan and brown fond forms around pan edges, 10 to 12 minutes. Add wine and cook until thick and syrupy, about 1 minute. Add reserved tomato juice and bring to simmer; reduce heat to medium and cook, stirring occasionally and loosening browned bits, until sauce is thick, 8 to 10 minutes.

Step 4

Transfer sauce to food processor (or transfer to saucepan and insert immersion blender) and add reserved tomatoes; process until slightly chunky, about eight 2-second pulses. Return sauce to skillet and add basil and extra-virgin olive oil and salt, pepper, and sugar to taste.