ANCHORAGE, Alaska (AP) — A serial killer who admitted he was responsible for the deaths of five Alaskans, including committing the first when he was only 14, has died in an Indiana prison, officials said.

Joshua Wade, 44, was found unresponsive in his cell June 14, Brandi Pahl, a spokesperson for the Indiana Department of Correction, said in an email Friday.

“Despite life-saving measures being performed, he was pronounced dead,” she said.

An autopsy was to be performed after Wade died at the Indiana State Prison in Michigan City, Indiana, to determine the cause of death. An email sent to the La Porte County, Indiana, coroner was not immediately returned Friday.

Wade was convicted of state and federal crimes in 2010. He was serving his term at Spring Creek Correctional Center, a maximum-security prison in Seward, Alaska. Four years later, he struck a deal to be moved to a federal prison in Indiana in exchange for admitting to additional deaths.

In 2000, Wade was charged with killing Della Brown by striking her in the head with a large rock. Her body was later found in a shed. However, a jury convicted him only of witness tampering and acquitted him on murder and sexual assault charges.

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Shortly after serving the sentence for tampering, Wade bound, gagged, kidnapped, tortured and then shot his neighbor, nurse practitioner Mindy Schloss, in a wooded area near Wasilla in 2007. He faced state and federal charges.

Wade entered into a plea agreement. He received life sentences for both state and federal charges in the Schloss killing and admitted to killing Brown. The plea meant he wouldn’t face the death penalty if a federal jury convicted him. The state of Alaska does not have capital punishment.

Wade was sentenced in separate proceedings Feb. 17, 2010, in state and federal court. At both appearances, he apologized for his crimes.

In state court, he said, “I deserve much worse. I’m sorry,” while turning to look at family members of the two murdered women.

In federal court, he reiterated the apology but then got in an angry exchange with U.S. District court Judge Ralph Beistline.

“What an evil thing you’ve done,” Beistline said. “What kind of person could take pleasure in the random destruction of another life?”

Beistline then described Wade as heartless, selfish and a coward.

At that point, Wade told the judge in an angry voice, “Don’t push it, man.”

The judge responded, “I’m going to push it.”

Beistline said Wade’s angry outburst was “very revealing” and said that type of anger could have been one of the last things Schloss experienced, and underscores what a danger Wade would be if free.

After serving four years at the Alaska prison, he struck another deal with prosecutors that would get him transferred to a federal prison in Indiana. In exchange, he admitted to killing John Michael Martin in 1994, when Wade was 14, and Henry Ongtowasruk, 30, in 1999. Wade also told prosecutors he killed an unidentified man on the night he killed Brown.

Then-Alaska Assistant Attorney General John Novak told The Associated Press at the time that by allowing Wade to transfer to the federal prison, Wade would dismiss a post-conviction relief case, meaning he would never get out of jail.

“In my evaluation, that’s an important benefit to the people, to make sure that conviction stays in effect,” he said. Novak noted that juries are unpredictable, and he pointed to Wade’s acquittal in the Brown murder case.

Novak said he didn’t care where Wade served his sentence as long as he served it.

It wasn’t immediately known when and why Wade was transferred to the Indiana State Prison from the federal facility in Terre Haute.