Can I wrap these operations in a single transaction using the available classes in the 3.5
framework?
No, and not with ANY other technology as you have a weak link.
1.Upload multipage tiff file to server using HttpPostedFile
2.Insert record of posted file to database
3.Process and save individual images in multipage tiff as individual files on server
4.Insert record of individual images to database
2-4 can be done easily in a transaction on a modern windows - NTFS can participate in a transaction.
Your problem is 1. 1 is impossible because - attention - HTTP HAS NO CONCEPT OF A TRANSACTION. If the upload happens from your server you COULD have upload instructions in an Upload CRM (Compensating Resource Manager) but you need to be able to delete them via HTTP too in case of a rollback and (perfectly, but optional) have them uploaded but not visible until you commit. This is IF THE API SUPPORTS IT - trivial to write (CRM in .NET is quite easy), otherwise you have a dead end there or take a compromise.
If you talk to upload TO your server then processing in a transaction, then technically to handle multi image uploads properly you have to decide where transactional control resides. The upload MUST have a proper API to start a transaction, do the uploads with a transaction token, then commit when all uploads are done (because only then processing can start). This is trivial to program - and does not even use TPM for most cases as you can roll logical transactions in your processing. but if you wan, again a CRM can handle the necessary changes in case of a rollback.