Interesting idea, it seems like you've done the research. I wish I could comment on it to add more information, but I'm in the same boat as you.

Has anyone else looked over the chemistry of this?

Good luck with your endeavor, hopefully these papers will be useful to you

A Novel Sequential Aminodiene Diels?Alder Strategy for the Rapid Construction of Substituted Analogues of Kornfeld’s Ketone

Through a novel sequence of aminodiene Diels?Alder reactions, amidofurans 18a?c were converted to tricyclic ketones 21a?c in moderate to good yields. Ketone 21a could be converted to Uhlé's ketone (6) by cleaving the tert-butyl carbamate and oxidatively removing the methyl ester. Tricycle 21a readily underwent bromination to give 22. Formation of the corresponding enol triflate 25 followed by carbonylation gave ester 27, which was then coupled with N-methyl propriolamide to furnish 26.

Sequential Aminodiene Diels-Alder Approach to the Ergoline
Skeleton
Through a novel sequence of aminodiene Diels?Alder reactions, several substituted amidofurans were readily converted to tricyclic ketones in good yield. The formation of the tricyclic ketone system is the result of a ring opening and dehydration of a transient oxabicyclic adduct formed by an intramolecular Diels?Alder cycloaddition of an amidofuran with a cyclohexenone moiety tethered such that it participates in the cycloaddition as the 2? component. A convenient way to construct the cyclohexenone is to make use of some aminodiene chemistry developed by Rawal. An angular carbomethoxy group is required in order to activate the olefin toward cycloaddition with Rawal's diene. The presence of this activating group not only prevents the isomerization of the advanced ergoline intermediate to a naphthalene but can also be leveraged for an oxidation to provide Uhle's ketone (13). The easily formed Kornfeld ketone analogue 25 was readily transformed into the corresponding triflate 41 by the action of triflic anhydride and a base. Oxidative addition of vinyl triflate 41 to Pd(0) and the ability of the resulting vinyl palladium species to undergo cross-coupling with terminal alkynes prompted us to devise an expeditious route to lysergic acid. Unfortunately, our inability to carry out a regioselective Heck reaction using vinyl triflate 41 and the methylene amino acrylate ester 48 thwarted the completion of the synthesis of lysergic acid.

The alcohol can be dehydrated by P2O5 and MeSO3H in 95% yield according to Rebek, and I bet there are methods in the literature.

Thanks for the references, I already got em though Ran a few numbers and the illustrious Dr. Rebek's method of getting to the ketone is the most practical: Tryptophan, Pd/C, H2, (60-70% yield) then Ac2O, AcOH and AlCl3 in DCM (57% on top of that). Later on MnO2 dehydrogenation at 75% yield, even then I think it's better. But the nitrogen has to be alkylated separately too. Instead of benzoyl, propionyl protection on the amines might be easier.

I toyed around with starting from indole as well: acrylic acid condensation to the 3-propionic acid (up to 69%  90% if you recycle the indole), and if you protect the indole nitrogen (pivaloyl, for steric reasons), there's a nifty procedure using AlCl3 and propionyl chloride to cyclise it at moderate yield. Alpha halogenation, somehow and that's bound to be indiscriminate, and then reaction with methylamine there ya go, and one doesn't have to mess around with hydrogenation/dehydrogenation. But that's more steps with somewhat less accessible reagents.

It would be really damn cool if methacrylic diethylamide and butyllithium could be used, for obvious reasons. But the other option would be using the wittig reagent derived from commercial bromomethyl methyl acrylate (avoiding the issue of dehydrating the alc). If the diethylamide isn't a strong enough EWG which is possible, then that would probably be the best route anyway. (And from the ester to the amide later on). I didn't think dry ice and acetone would be quite so bad, now that you mention it it could be a pain.

The manganese cyclisation should be fine though. Only thing that keeps me up is that it doesn't work on pyrrolidine at all, very strange. There is also precedent for using K2CO3 on MgO for that kind of addition with high yields with methyl acrylate and aliphatic amines, although not cyclisation afaik. Still reading up on this type of thing, apparently various catalysts have been used.

It probably would lead to some iso-lsd. Chromatography would sort that out, but there might turn up a stereospecific method. Some kind of co catalyst with the MnCl2 sounds possible but I have no idea.

[edit] After some reading, it might even be possible to get by using methyl methacrylate directly (for the lithiation) as long as the reaction were kept short and sweet; but the amines would have to be well protected and the yield would be lower. Methacrylic acid itself might work, I thought I've seen the dianion mentioned but I can't seem to find the ref again.

I feel like im constantly being the nay-sayer around here...
just looking at your starting compound raise a red flag! alpha-aminoketone... thats always a bad idea. especially if you plan to use a base (and you do)... dimerization/double molecule cyclization should ring in your ears! if it doesnt, i suggest going back to the textbooks and reading up on functional groups and their reactions.
Another point i feel i should mention, which is present in the old literature, in articles dabbling in ergolines total synthesis, is that the D ring cyclization is quite hard and does not proceed easily. from what i know, i would wager that what you will get is a 5 membered ring protruding to the right in your picture, instead of your wanted 6 membered ring.

also, do you have any real life experience with t-BuLi? that is one of the nastiest reagents ive had the displeasure of working with. It is a serious hazard!
One of our emeritus professors has lost an ear and his nose from a BuLi mis-hap. It catches fire super easily, it is hard to extinguish.
It is absolutely impractical to work with it outside of the lab, and even in the lab, i would never consider carrying even a moderate scale reaction with BuLi!!!!!! Be Warned!

nBuLi is usually added via a syringe.  It's not uncommon to see sparks on the end of the syringe from the reagent. sec-buli on the other hand is less reactive and will "only" ignite paper, cotton, clothes etc.

On the MnCl2 thing, ahah!? The angles don't make sense with the unsaturated bond there, that's why it's so difficult to close. The key must be to dehydrate the alcohol AFTER the ring is formed. Now what exactly is the mechanism of that catalysis... I was thinking intermediate is a 3 member ring with Mn and the electron deficient alkene (does that sound right? It's the only thing I could sketch out that made any sense). That might violate Baldwin's rule, but then "cations are often exceptions" it says, so I don't know. (And the momentary primary cation would be what does the job, being why the EWG is so important) The whole thing hinges on the final cyclisation of course.

Sorry for the uneducated musings, haha, I never said I was an expert!

Ill have a look at the Mn mechanism and see what i can learn from it. Will report back.

Thanks! I really appreciate the help, and "naysaying".

Leaving that amine protected and hydrolysing it afterwards is the solution to that trouble, hopefully.

You could probably get away with mere alkylation of the tryptophan amine considering methylone is at least reasonably stable. You're going to end up alkylating it eventually anyway; the most interesting groups (to me) that can go on there are methyl and allyl, the former giving rise to classic LSD and the latter giving rise to AL-LAD which of all the lysergamides in TiHKAL seems to be a clear winner as far as I can tell.

The most interesting thing about this route of yours is the ease to which it seems to lend itself to making the other various 6-substituted lysergamides such as ETH-LAD, AL-LAD, PRO-LAD etc.

Tangentially, there is a procedure using Fremy's Salt to simultaneously dehydrogenate an indoline in good yield and hydroxylate where the 5-position on an indole would be, but I doubt anybody would want to do that. Who knows, it might not be active at all, could be even more active if that's possible, it could even be a disproportionally potent, ie fatal vasoconstrictor. But Fremy's Salt would probably make it.

edit - there was a revised proposal here, some flaws became apparent so now I'm removing it. If only it were that simple with real cholesterol.

The lamentation is that after doing some research (why oh why is it so hard to ask the right questions?) it seems that  5-aminopentenes are more apt to cyclise to the 5 member ring

The only possible saving grace would that relatively weak e- withdrawing diethylamide, and maybe the MnCl2 catalyst. I can't find anything on MnCl2 in the context of intramolecular hydroamination, and the amide is on the 2 of the 5-aminopentene, whereas it would do the most good on the tail, 1. At least as far as a reference from a dissertation on Fe catalysis is concerned.

So it's a guess, but not as bright a one as I'd hoped. Shame, the procedure was so simple.

Although, I wonder, would an amide of the "wrong" product this implies be active at all? It's not unthinkable.

Bluebottle, could you explain the second step (Ac2O, AcO, AlCl3)? I can't figure out the mechanism. I even tried to figure it out with models and couldn't figure out how the intermediate goes to the final product.

Sorry, I'm a bit under-educated for this level of chemistry, but this synthesis looks very interesting.