Scottish entrepreneur Sir Tom Hunter was last night confident of winning his fight to retain a stake in the Wyevale garden centres business that was at one point a key piece of his investment strategy.

But Hunter's investment vehicle West Coast Capital appears to have given up on at least one investment in a housebuilder and is cautious about retaining a stake in another.

Hunter is thought to have a 40% stake in Wyevale which was taken private in 2006. But it is in talks with Edinburgh-based HBOS, long Hunter's lender of choice, about a debt-for-equity swap to safeguard its future. It has debts of around £360m. The retail sector has been particularly badly hit by the economic downturn.

A spokesman said of the Wyevale talks: "Whilst those negotiations are ongoing and positive they have not yet concluded but we are confident we will conclude negotiations and retain a major shareholding in that business which will be well financed going forward - those negotiations may or may not conclude before Christmas."

Hunter's stake in Wyevale at one point gave him the opportunity to merge the business with other com- panies in which he had substantial holdings.

He already owns Blooms of Bresingham and has a near 30% stake in Flying Brands, the mail order flowers company, although he abandoned a takeover attempt there last month. He also had a 29.4% stake in rival garden centre chain Dobbies, although he was relieved of this at a loss earlier this year after losing a court case to majority shareholder Tesco.

Hunter's housebuilding investments are also turning sour as the plummeting housing market takes its toll. Hunter confirmed yesterday that he had written off his entire remaining equity stake valued at around £35m.

West Coast Capital and HBOS were thought to have had 50-50 ownership of the takeover vehicle that bought Crest Nicholson for more than £700m in 2007.

He has more hope of retaining a stake in McCarthy & Stone which he bought as part of a £1bn consortium, again with backing from HBOS.

"As to McCarthy & Stone we have written down our stake in that business but negotiations continue and we may or may not retain equity in that business where we currently have a minority 8% equity stake; predictions on the outcomes of negotiations are entirely speculative."

HBOS is thought to hold a 20% stake in the business, which has struggled to raise cash as the property market has plummeted.

Hunter is also exposed to the economic downturn through his other retail investments. He has an 11.1% stake in Jenners owner House of Fraser in which HBOS and troubled Icelandic investor Baugur also have large stakes. Office, the high street shoe store, is thought to be doing well but USC, the branded clothing business, is thought to be struggling.

The difficulties at these companies marks a notable downturn in the fortunes of the man who was once valued at more than £1bn and ranked as Scotland's richest man. Hunter's most notable success was in building clothing chain Sports Division before selling it to JJB Sports for £290m in 1998.

His wealth has dropped to such an extent that this week Jim McColl of Clyde Blowers felt able to claim the title of Scotland's wealthiest individual, claiming he now has personal wealth of £800m while Hunter is getting by with £750m.

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