Here is what I had to do (using the example points/plane above):
//rotatation origin
CGPoint rotateOrigin = CGPointMake(0,0);
//rotatation transform
CGAffineTransform translateTransform = CGAffineTransformMakeTranslation(rotateOrigin.x, rotateOrigin.y);
//rotate the plane 90 degrees
float radians = 90 * (M_PI / 180);
CGAffineTransform rotationTransform = CGAffineTransformMakeRotation(radians); CGAffineTransform customRotation = CGAffineTransformConcat(CGAffineTransformConcat( CGAffineTransformInvert(translateTransform), rotationTransform), translateTransform);
CGAffineTransform m1 = CGAffineTransformIdentity;
CGPoint startPoint = CGPointApplyAffineTransform(CGPointMake(200,200),m1);
//rotated point
CGPoint rotatedPoint = CGPointApplyAffineTransform(startPoint, customRotation);
//final rotated point- after adjusting for the rotation
rotatedPoint = CGPointApplyAffineTransform(rotatedPoint, CGAffineTransformMakeTranslation(500,-500));