Chris Froome’s hopes of winning the Vuelta a Espana are all but over after he sustained heavy losses on a brutally mountainous 11th stage won by breakaway rider Mikel Landa.
Froome (Team Sky) crashed early in the stage and was then dropped on the fourth of the day's six climbs, eventually crossing the line 7min 19sec behind Fabio Aru (Astana), who took the race lead by finishing second.
It leaves Froome 7min 30sec adrift of the red jersey and means he will almost certainly be unsuccessful in his bid to become only the third rider in history to complete the Tour de France-Vuelta a Espana double.
The 30-year-old Briton was limping heavily when he dismounted his bike at the end of the stage and was later taken to hospital for X-rays.
Aru, meanwhile, attacked twice on the final climb to Cortals d'Encamp to finish 1min 22sec down on team-mate Landa and, crucially, 1min 37sec ahead of previous race leader Tom Dumoulin (Giant-Alpecin).
The result was enough to elevate him into the race leader's red jersey and open up gaps of 27 seconds over second-placed Joaquim Rodriguez (Katusha) and 30 seconds over Dumoulin, who is now third.
Froome was not the only big-name rider to suffer on one of the hardest grand tour stages ever devised, as Alejandro Valverde (Movistar) and Nairo Quintana (Movistar) lost 1min 42sec and 2min 57sec to Aru respectively.
Valverde is now 1min 52sec off the lead in sixth, while Quintana's chances of overall victory look remote after he fell to 3min 7sec down in ninth. Froome was relegated to 15th.
After the stage, Geraint Thomas (Team Sky), who stayed with Froome, toldEurosport: "He obviously had a heavy crash and he said his foot was quite bad. He said his legs were OK, but on that especial-category climb, the fourth climb, he started to suffer and when Astana really lit it up, he got dropped.
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Froome was taken for X-rays after the stage
"I was about to get dropped myself anyway, so I sat up and waited for him. He seemed to come around on the last climb but we just had to keep going. He always keeps fighting and that's what we did. Not the ideal day.
"Froomey keeps fighting and he is still in the race, so he can go for stages or whatever. Obviously it's disappointing to be out of the GC now. Not a good day for Froomey."
Landa formed part of the day's 19-man breakaway but attacked at the foot of the final climb and never looked in danger of being denied a Vuelta win to go with the two stage victories he took at May's Giro d'Italia.
Back down the road, and with Froome out of the picture, all of the remaining race favourites started up the final climb together, but then Aru attacked with about 8.5km to go and only Rodriguez and Daniel Moreno (Katusha) could follow.
Aru dropped the pair with a second attack 2km later and continued to set a fierce pace as he looked to overhaul his 1min 13sec deficit to Dumoulin at the start of the day.
Dumoulin was initially dropped by a chase group containing all of the other race favourites, but he later caught back up to them and then even distanced both Valverde and Quintana as his remarkable climbing form at the Vuelta continued.
The race continues on Thursday with a 173km 12th stage from Escaldes-Engordany to Lleida, which should end in a sprint.
Stage 11 result
1 Mikel Landa (Esp) Astana, 4:34:54
2 Fabio Aru (Ita) Astana, +1:22
3 Ian Boswell (USA) Team Sky, +1:40
4 Daniel Moreno (Esp) Katusha, +1:57
5 Joaquim Rodriguez (Esp) Katusha, +1:59
6 Rafal Majka (Pol) Tinkoff-Saxo, +2:10
7 Mikel Nieve (Esp) Team Sky, +2:10
8 Esteban Chaves (Col) Orica-GreenEdge, +2:59
9 Tom Dumoulin (Ned) Giant-Alpecin, +2:59
10 Diego Rosa (Ita) Astana, +3:02
General classification
1 Fabio Aru (Ita) Astana, 43:12:19
2 Joaquim Rodriguez (Esp) Katusha, +27
3 Tom Dumoulin (Ned) Giant-Alpecin, +30
4 Rafal Majka (Pol) Tinkoff-Saxo, +1:28
5 Esteban Chaves (Col) Orica-GreenEdge, +1:29
6 Alejandro Valverde (Esp) Movistar, +1:52
7 Daniel Moreno (Esp) Katusha, +1:54
8 Mikel Nieve (Esp) Team Sky, +1:58
9 Nairo Quintana (Col) Movistar, +3:07
10 Louis Meintjes (RSA) MTN-Qhubeka, +4:15
