The amide moiety on lysergic acid amide has a pKa of about ~17 (I don't know this, really, I'm just assuming it's similar to acetamide) and can be deprotonated in strongly basic conditions -- as long as they are dry enough to prevent hydrolysis. While alkylating an amide is difficult, alkylating the conjugate base of an amide is (presumably) not, and should be possible with a typical alkylating agent such as diethyl sulfate or diethyl carbonate. Haloalkanes are unsuitable, since they will dehydrohalogenate in the strongly basic reaction conditions. A suitable base might be lithium isopropoxide, available from the reaction of lithium with dry isopropanol. Lithium tert-butoxide would be absolutely superior, or perhaps lithium 2-methyl-2-butoxide, since 2-methyl-2-butanol is possibly easier to obtain via RC sites than tert-butanol via chemical suppliers, and RC suppliers aren't in bed with the DEA. Lithium alkoxides can be prepared by reaction of the alcohol with lithium.

So, the idea is LSA + ROLi + Et2SO4/Et2CO3/Et3PO4 ---> LSD.
Since LSD inverts in the presence of base, it would produce a racemic mixture of LSD and iso-LSD, the latter of which is inactive -- but it's better than no LSD at all, I say. Further, the LSA present in most plants is already racemic, so inversion is not really a concern.

I don't know how well this would work, because amide conjugate bases are essentially unknown in the literature. There's almost nothing out there about them -- are they unstable for some reason I don't know?

Does this sort of route have any potential at all?

How about ethyl pyruvate? It should be more reactive than a typical ester, similar to ethyl oxalate, but the production of ethyl pyruvate doesn't involve worrying about the mono-alkylated side product as you would with ethyl oxalate.

We need more discussion on this. Please discuss.

Ok, so are you suggesting that there is a method from LSA amides (including all the ones that could or would be active/iso) to LSD?