Commentator John N. Oswalt (NICOT-Isaiah, Vol I, pp. 349-50) had no such problem with the fulfillment of this prophecy:
After dealing with Judah's southern neighbors, Philistia and Moab [in chapter 16], Isaiah now turns to address the two to the north[, the ten tribe kingdom of Israel and Syria]. Although the oracle is addressed to Damascus, the main focus after v. 3 is upon Northern Israel. This combined treatment suggests that the prophecy is one of the earlier ones, having originated during the Syro-Ephraimite alliance in 735-732 [Note: Real dating, not the Society's dating. The Society has Ten-Tribe Israel as having fell in 740 BC.] . . .
1, 2Damascus was one of the most strategic cities of the ancient world, for it stood at the mouth of a natural funnel through which ran the only convenient land route between Mesopotamia and Egypt. North of the city stands Mount Hermon and south of it are a series of basalt plateaus. Both of these constitute barriers to caravan travel. As a result, Damascus exercised an influence far beyond other cities of comparable size. Yet Isaiah says that Damascus will be turned from a city into a ruin. By the time of the prophecies against Philistia and Moab [in chapter 16], this prophecy had already come true in large part, as Shalmaneser had conquered it after a ruinous siege in 732.
[End of quote. Material in "[ ]" is Bobcat's for clarification.]
The strategic location of Damascus would ensure that it was a natural place to rebuild the city afterward. The prophecy makes no mention of how long it would be desolated.
Perry, I'm curious. Are you looking for a modern day repeat in connection with an Israeli-Syrian conflict?
The recent introduction of Russian S-300 AD missles and a dozen+ Russian warships has made things very interesting for the West. Russian air defense and anti-ship systems are very dangerous to Western air and carrier battle groups and offer a very wide area of coverage. The Israelis are having a fit about the S-300 because it has the potential to nullify Israeli airpower.
The Russians have also developed a number of shipping container systems that are potentially lethal to air, sea, and ground based forces. These could very easily be in the country without the West/Israel knowing about them.
Putin seems to have drawn a line in the sand. Not sure if they are putting boots on the ground or not. Probably advisors and training personnel, at the least. People looking for apocalyptic implications are putting up many YouTube videos.
Take Care