Im not a pro but it sounds like your motor was built to run high octane and by using 87 octane, you made it detonate from the first bang. Im guessing it was detonatin so bad that the fuel was becoming unstable long before TDC and pre-ignighting the fuel, meaning when it was time for the spark to normally ignight it, you had no fuel or very little left to burn. You would have slowly been chipping away at your pistons, causing them to leak and lower your compression and crank case pressure, also causing power to drop fast.