Yes, it should be possible... at least, rotating the 8x8 blocks is easy. The problem arises with the coefficients inside the block. A 90º rotation is also a 90º rotation in the frequency domain (fourier, or dct), so that is not hard. But, I'm not sure that the lossy compression always keeps "simetrical" coefficients, or it has a prefered direction. I would say that some of them, after the rotation, will fall on ignored positions, so at the end we'll have either loss of data, or/and artificial coefficients (= zero?).
Please correct me if I'm wrong.