Pablo Picasso's Tete a L'oiseau is expected to make $2m-3m at Sotheby's contemporary art day sale on November 6.
Picasso painted the work in 1971, when he was in his late 80s.
The work was inspired by Picasso's many mistresses
Sotheby's explains how the work appears to be an amalgamation of the artist's love interests: "Picasso's mistresses were the inspiration for many of the paintings and drawings of women that he completed throughout his career�Ǫ
"This striking picture from 1971, however, seems to be a composite of the many women who enriched the artist's life while also suggestive of the artist's own personage�Ǫ
"One can only guess that Picasso, who would turn ninety in September of that year, may have been driven by nostalgia to incorporate into this painting all of the great loves of his life."
Joan Miro's Femme et Oiseau III/X is likely to prove another highlight, with a valuation of $1.5m-2m.
The work is one of a series of 10 the artist painted on burlap in 1960.
Miro was a Spanish artist associated with the surrealist movement. His highly distinctive work was a major influence on the abstract expressionists.
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