Sir Tom Hunter, the Scottish entrepreneur and philanthropist, is set to hand over a large part of his shares in debt-laden Wyevale to HBOS, the garden centre chain's lender, by Christmas Eve. The Times has learnt that the debt-for-equity swap will give the bank about 45 per cent of Wyevale's shares, leaving Sir Tom out of pocket on another HBOS-backed buyout. HBOS and Sir Tom declined to comment.

Sir Tom, who promised last year to give £1 billion to charity over his lifetime, took a big gamble on the property market in 2006 and has since lost millions of pounds. The Scot is one of a number of high profile businessmen including Robert Tchenguiz and Sir Philip Green who were backed by Peter Cummings, HBOS's corporate chief. Mr Cummings, whose division is currently writing off its investments at the rate of £37 million a day, is set to leave the bank with a controversial payout as soon as its merger with Lloyds TSB is finalised in January.

Sir Tom's West Coast Capital private equity vehicle is likely to lose all it invested in McCarthy & Stone and Crest Nicholson, the housebuilders it took private in 2006 and 2007. McCarthy & Stone, a retirement home builder for which West Coast paid £1.1 billion, has been in breach of its bank covenants for months. A source close to McCarthy & Stone's lenders, which are in talks to restructure its debt, told The Times they intend to force through a debt-for-equity swap next month that will wipe out Sir Tom's investment.

A source close to West Coast, which owns 8 per cent of McCarthy, said Sir Tom has written off some of his investment, but hopes to salvage something.

Management and leading lenders to Crest Nicholson have agreed a restructuring plan. It will see the lenders seize 90per cent of the company in return for halving its £1 billion debt mountain, meaning the Scottish entrepreneur will lose all the money he invested in his leveraged £715 million buyout. Sir Tom has never revealed how much equity he put into Crest, but he and HBOS are the company's only shareholders.

Talks over the fate of Wyevale, a garden centre chain with 122 stores taken private by Sir Tom in 2006, have been more straightforward. The company is controlled by Sir Tom, who has 40 per cent of the shares, and HBOS, which has 19 per cent and is the only lender. The restructuring is to be finalised, but it is thought HBOS will write off much of the £370 million it lent Wyevale in return for easing the company's debt covenants under the restructuring.

Negotiations over the fate of McCarthy & Stone, where Sir Tom's buyout consortium included high profile investors such as Richard Desmond, owner of the Daily Express, the property magnates Simon and David Reuben and property developer Nick Leslau, have been more complicated.

The company's structure relies on complex financial engineering with several tranches of senior debt and subordinated mezzanine debt owned by banks, investors and hedge funds. McCarthy & Stone broke the senior debt covenants, but lenders gave a waiver.

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