You may be able to include a stop in Juneau and Anchorage but Kotzebue and Barrow would be out of the question - they only have service from Anchorage and aren't on the way to any other AS destination in the state of AS.

Boston flights are running at just about 80% load factor so it's very possible that there wouldn't be any award space at this point but I would check back as it changes from time to time as the re-evaluate the market. Good luck and enjoy.