Drain the tomatoes in a fine-mesh strainer set over a large bowl. Open the tomatoes by hand to remove and discard the seeds and fibrous cores, then let them drain for 5 minutes. Set aside a small portion of the tomatoes and reserve the required amount of tomato juice, discarding any extra.

Heat most of the oil in a 12-inch skillet over medium heat until shimmering. Add the onion and cook until softened and lightly browned, 5 to 7 minutes. Stir in the garlic and oregano and cook until fragrant. Add the main portion of drained tomatoes and increase the heat to medium-high. Cook, stirring often, until the liquid has evaporated and the tomatoes begin to brown and stick to the pan, 10 to 12 minutes—this browning is essential for a deep flavor.

Stir in the wine and cook until thick and syrupy, about 1 minute. Add the reserved tomato juice and scrape up any browned bits from the bottom of the pan. Bring to a simmer and cook, stirring occasionally, until the sauce is thickened, 8 to 10 minutes.

Transfer the sauce to a food processor, add the reserved whole tomatoes, and pulse until slightly chunky, about 8 pulses. Return the sauce to the skillet, stir in the basil and the remaining oil, and season with salt, pepper, and sugar to taste. Serve hot with pasta, adding a splash of pasta cooking water if needed to adjust the consistency.