The High Court has ordered the appointment of a liquidator to three companies controlled by developer and hotelier Hugh O'Regan.
Mr O'Regan is best known for founding the Thomas Read Group of pubs, which he sold four years ago for €30m.
The court took the step after an interim examiner, appointed to the companies last month, found they do not have a reasonable prospect of survival.
The examiner was appointed after Anglo Irish Bank began the process of having a receiver appointed to two of the companies.
Counsel for the three companies Bernard Dunleavy told the court that when the interim examiner was appointed to Thomas Read Holdings, Dashaven and Clubko last month, the companies and the independent accountant believed they had a reasonable prospect of survival.
But, he said in the interim, the companies had been in touch with their various financiers, and it had now become clear that is not the case.
This was also the view of the interim examiner appointed by the court, Mr Dunleavy said.
Anglo Irish Bank is owed over €80m by Mr O'Regan's various companies.
Around €20m of that debt is owed by Thomas Read Holdings and Clubko.
Irish Nationwide Building Society is owed almost €180m by Dashaven, which is the company responsible for the redevelopment of the former Kilternan Hotel and Country Club in Dublin.
Clubko owns the former Hibernian United Services Club at 8 St Stephen's Green, which it had intended redeveloping as a new private members club.
Thomas Read Holdings is a holding company for a variety of Mr O'Regan's interests, including the Morrison Hotel, which will not be immediately affected by today's liquidation order.
Thomas Read Holdings also owns a property at 4 Parliament Street in the city.
Today's application for the appointment of a liquidator was opposed by Anglo Irish Bank, which had previously sought the appointment of a receiver to two of the companies, and opposed the appointment of an examiner.
Counsel for Anglo Irish Rossa Fanning said the development was a truly remarkable volte-face by the companies.
He said it was unnecessary to appoint a liquidator to Thomas Read Holdings and Clubko, as the receiver previously appointed by the bank could do the same job.
Mr Fanning also argued the court did not have jurisdiction to appoint a liquidator.
A similar argument was made by counsel for Irish Nationwide Building Society, who said that the building society was the only creditor of Dashaven.
He claimed the society has a receiver ready to act, and added that liquidation was an unnecessary and expensive option.
After considering the matter, Mr Justice Garrett Sheehan said he saw no significant downside to acceding to the companies' request.
He made an order winding up the three companies, appointing Kieran Wallace of KPMG as liquidator, and he lifted the court protection from the businesses.