Mikel Landa won the 11th stage of the Vuelta a Espana while his Astana teammate Fabio Aru assumed the overall lead as Chris Froome suffered a crash that dropped him down to 15th.
Froome crashed out on the first climb of the stage, suffering a cut to his right leg. The British rider was able to continue a demanding day's racing that contained six mountain passes, but could not make ground on the leaders.
He finished the day 15th on both the stage and in the overall classification, seven minutes and 30 seconds behind the new red jersey, Aru.
Astana's Landa clinched the 138-kilometre route from Andorra la Vella to Cortals d'Encamp, the toughest stage to ever feature in the Vuelta, in four hours, 34 minutes and 54 seconds.
Italy's Aru crossed the line 1min and 22secs behind to finish second while American rider Ian Boswell of Team Sky came in third.
Aru leads the general standings by 27 seconds ahead of Spain's Joaquim Rodriguez, who came home 1:59 behind the stage winner.
Giant-Alpecin's Tom Dumoulin, who went into Wednesday's stage as the race leader after Tuesday's rest day, has dropped to third in the general standings and the Dutchman is now 30 seconds adrift of Aru.
Tinkoff Saxo rider Sergio Paulinho was forced to withdraw from the race after colliding with a TV motorcycle. The Portuguese rider was taken to hospital and needed 17 stitches in his leg.
Thursday's 12th stage is a 173km ride from Escaldes-Engordany to Lleida.