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Mr Entwisle said there was a danger some of the character of the underappreciated example of ''glass and steel modernism'' could be lost when the university embarked on its ambitious plan to renovate and add to the 1961 Walsh Building in Great King St.
This comes as university chief operating officer John Patrick revealed more details about the project, which included demolishing the building's west wing and erecting a new clinical block in its place.
The plan, which was approved last week, would cost less than a new building, but would take longer to complete, Mr Patrick said.
Mr Entwisle was not worried the 1980s-built west wing - which sits behind the original Walsh Building - was being demolished, as it was not in keeping with the rest of the building.
''That last addition was just crude. It's a B-grade addition to an A-grade building.''
He believed the university faced a difficult task balancing the needs of a modern dental school and retaining the character of the New Zealand Historic Places Trust category 1 historic building.
''It is a very fraught project. Exactly how they go about adding on to, or building around the 1961 building, that will be the test of how successful everything is,'' he said.
While the building was largely disliked by citizens, it was one of the best examples of ''glass and steel modernism'' in New Zealand.
Property services director Barry MacKay said a decision last week to go with a new architect to lead the project was not due to a falling-out with the previous architect.
With the project on hold since the beginning of last year, the university decided to ''have a fresh look at the design options by retendering the lead architectural services'', Mr MacKay said, noting ''the original lead architect participated in that process.''
Otago University Faculty of Medicine dean Prof Peter Crampton said: ''This major upgrade will ensure the school can continue to enhance its considerable strengths in research, education and providing healthcare to New Zealanders,'' he said.