Plovdiv city was possibly at times a vassal of Bulgaria or Venice. Ivan Asen II conquered the duchy finally in 1230 but the city had possibly been conquered earlier. Afterwards, Plovdiv was conquered by Byzantium. According to some information, by 1300 Plovdiv was a possession of Theodore Svetoslav of Bulgaria. It was conquered from Byzantium by George Terter II of Bulgaria in 1322. Andronikos III Palaiologos unsuccessfully besieged the city, but a treaty restored Byzantine rule once again in 1323. In 1344 the city and eight other cities were surrendered to Bulgaria by the regency for John V Palaiologos as the
Plovdiv European mosque outside Moorish Spain. The Sephardic Plovdiv Synagogue is at Tsar Kaloyan Street 13 in the remnants of a small courtyard in what was once a large Jewish quarter. Dating to the 19th century, it is one of the best-preserved examples of the so-called "Ottoman-style" synagogues in the Balkans. According to author Ruth E. Gruber, the interior of the Plovdiv Synagogue is a "hidden treasure…a glorious, if run-down, burst of color." An exquisite Venetian glass chandelier hangs from the center of the ceiling, which has a richly painted dome. All surfaces are covered in elaborate, Moorish-style, geometric designs in