I was reading through some of the information on Mike's technology when I put 2 and 2 together and came to the realization that is was possible for a modified Star Trek ship to take down an ISD's shields. What lead me to this conclusion was the following information taken from the Empire Shield's page
this means that the energy capacity of a Star Destroyer's shields is between 1.4E19 and 9E20 joules, so 1E20 joules (24,000 megatons) is a reasonable estimate.
and this information taken from the Federation Power Generation page.
Therefore, the storage density of antideuterium aboard a Starfleet vessel is less than or equal to 160 kg/m³, which is the density of solid (but not metallic) deuterium. At this density, the ship's 3000 m³ storage tanks should hold roughly 480 tons of anti-deuterium.
and
The theoretical energy density of the matter/antimatter reaction is 9E16 J/kg, so an upper limit for their energy yield is roughly 8.6E22 joules (roughly 900 TW average, over three years). This is more than eighty times as large as the 1E21 joule energy yield estimated for the total annihilation of the ship's entire fuel supply in its primary self-destruct sequence (TM pg. 141). The self-destruct sequence occurs in the warp core; the ship simply dumps its entire matter/antimatter storage into its warp core at once, so the limited yield of the self-destruct sequence may suggest poor efficiency for the warp core, perhaps as low as 1.3% (although Federation cultists are loathe to give up their ridiculous and unscientific 100% efficiency assumptions). It is possible that the efficiency of the self-destruct is so low precisely because so much fuel is being dumped into the warp core at once, but this means that we can establish that the range of efficiency is somewhere above 1.3% and somewhere below 100%.
At first appearance the energy generated from the self destruct of the 480 tons of anti-matter in the primary self-destruct sequence of a GCS is enough to take down the shields of a ISD (even with the low 1.3% reaction rate). However, we must consider the fact that even in an ideal detonating position no more then half of this energy will reach the ISD. Knowing this we can say that if a ship were modified to carry 960-1440 tons of anti-matter (in the same density as that found on a GCS) then it could take down an ISD's shields (assuming it could get through the fighter escorts and turbolaser fire). If the reaction rate were increased then the amount of anti-matter needed to achieve this feat would be signifigantly less or more damage would be caused by the same amount of anti-matter. After the shields are taken down it would be wise to repeat this strategy with more ship/s in an attempt to keep the ISD's shields down and destroy the ISD. How effective these secondary strikes would be is unknown; I do not know how strong the ISD's actual armor is, nor do I know where within the hull the shield generators are located. However, since Mike estimated the broadside of an ISD i'm going to go out on a limb and say that this sort of detonation would cause damage, perhaps even signifigant damage, to an ISD.
Characteristics of offensive weaponry. An ISD1 can unleash more than 6E19 joules (14,000 megatons) of energy with a full broadside.
It should be noted however, that even if the Federation, or more likely the Klingons, used this tactic and managed to achieve a 2 to 1 kill ratio against the ISD's (which is so improbable that the chances of this happening are practically zero) they would be no where close to winning the war. The Empires signifigant reasource advantage would still win the day for them. Finally, it should be noted that ST shields are very weak in comparision with SW weapons, and that it would be difficult at best for a ST ship to get close enough to pull off this tactic.
Devolution is quite as natural as evolution, and may be just as pleasing, or even a good deal more pleasing, to God. If the average man is made in God's image, then a man such as Beethoven or Aristotle is plainly superior to God, and so God may be jealous of him, and eager to see his superiority perish with his bodily frame.
-H.L. Mencken