Specialists say court decision could scare off international investors.
Alesco, whose tax-avoidance battle with Inland Revenue is seen as a test case for disputes involving more than $300 million, is trying to appeal to the Supreme Court.
Last month Alesco NZ lost another leg of its stoush with the IRD over whether a funding structure it used to buy two other companies was a tax avoidance arrangement.
In 2003 the Australian building products supplier used an arrangement known as "optional convertible notes" (OCNs) to advance $78 million to its New Zealand subsidiary for these purchases.
Between 2003 and 2008 Alesco NZ claimed deductions for amounts treated as interest liabilities on the notes, in accordance with a determination issued by the tax commissioner.