Syrian regime forces took full control of the key northwestern town of Khan Sheikhoun on Wednesday, surrounding Turkish forces at a nearby observation post, a war monitor said.
"Regime forces took full control of the town of Khan Sheikhoun and are currently clearing it of mines," said Syrian Observatory for Human Rights chief Rami Abdel Rahman.
Pro-regime fighters have now "surrounded an area stretching from the south of Khan Sheikhoun into northern Hama province, cutting off all roads out" for Turkish troops in the nearby town of Morek, he said.
The Observatory said 21 anti-government fighters including 18 jihadists were killed in Wednesday's clashes, along with 10 government or loyalist fighters.
The advance came after days of heavy fighting against rebels and jihadists who control the Idlib region, which sits on the Turkish border and is the last major stronghold of opposition to the Russia-backed Bashar al-Assad.
It has been administered since January by the Hayat Tahrir al-Sham alliance, which is led by jihadists from Syria's former Al-Qaeda affiliate.
The region of some three million people was supposed to be protected by a buffer zone deal signed last September by Moscow and rebel backer Ankara, but regime and Russian forces have subjected it to heavy bombardment since late April.
Around 890 civilians have been killed since then, according to the Britain-based Observatory.
In recent weeks, regime forces have inched forward at the southern edges of the bastion.
On Tuesday, anti-Assad fighters pulled back from Khan Sheikhoun and the countryside to its south, said the Observatory, which has a network of sources across Syria.
Wednesday's advance raises the stakes in a showdown between Syria and Turkey, whose Foreign Minister Mevlut Cavusoglu has vowed to "do whatever is necessary to ensure the security of our soldiers and observation posts".
Moscow claimed rebel attacks against a key Russian air base to the west of Idlib and on regime-held civilian areas had continued despite the presence of the Turkish posts.
The Syrian regime has accused Turkey of backing "terrorists", its term for both jihadists and rebels.
Retaking Khan Sheikhoun has long been a key regime objective, as the town lies on the highway connecting Damascus to second city Aleppo.
The regime's advance has pushed thousands of people to flee to Syria’s border with Turkey in the last few days.
They left Maarat al-Numan, a city in Idlib province that has been a sanctuary for families fleeing former rebel areas, as a Russian-led push has come close to capturing the strategic town of Khan Sheikhoun further south.
“The flow of cars and vehicles leaving is not stopping,” said Abdullah Younis from the city. Rescuers there said around 60,000 people had fled in the last four days alone.
A Turkish military convoy crossed the border into Idlib on Monday and headed south along the highway, drawing condemnation from Damascus.
Ankara alleged an air strike had targeted its troops, while a Syrian pro-regime newspaper said regime aircraft had targeted a rebel vehicle leading them.
The convoy was at a standstill on Wednesday just north of Khan Sheikhun, after government forces to the south cut the road into the town.
Meanwhile, Syrian opposition activists say regime airstrikes have hit a hospital in a rebel-held northwestern village of Tel Mannas, knocking it out of service. There was no immediate word on casualties.
The Britain-based Syrian Observatory for Human Rights and the Thiqa news agency, an activist collective, said the Rahma hospital in Tel Mannas was hit early on Wednesday.
Activists reported several airstrikes on Idlib, the last major rebel stronghold in Syria, as regime forces captured new areas from insurgents.
Eight years of war in Syria have killed 560,000 people and driven half the pre-war population of 22 million from their homes, including more than 6 million as refugees to neighbouring countries.
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