THC catalyst question

[goiterjoe]

ok, here's a reaction I was thinking about, and was wondering what would be a good catalyst for it:

pulegone + olivetol ---->  THC

from the limited patents I could find with similar reactions, a lewis acid such as ferrous chloride seems like it would work.  my organic chemistry is really lacking though, and was wondering if anyone else has some insight or guidance they feel like sharing. 

olivetol is supposedly contained in certain lichens, and pulegone is an extract from pennyroyal that I imagine can be distilled at low temperatures under really strong vacuum.  now, would the THC obtained from pulegone even be active in the brain without the double bond at the 9 position that makes delta-9-THC?  if so, would it be more active than the delta-9-THC, which can theoretically be made with olivetol and a citrus oil extract similar to pulegone but with the double bond?

personally I don't even like THC and don't care to make it, but I would really like to find out for a friend of mine who wants to know, and there are probably several people on the hive that would be interested.

If pacman influenced us, we'd glide around dark rooms eating pills and listen to repetitive music.

[terbium]

You can use all sorts of things to catalyze the condensation - formic acid, phosphorus oxychloride, sulfuric acid, toluene sulfonic acid, boron trifluoride probably even a sulfonated cation exchange resin. Never heard of using an iron salt. Different acids will give differing mixtures of condensation products.

I believe that pulegone and olivetol will give delta-3-THC (plus a lot of other stuff). Never heard of delta-9-THC, just delta-1 through delta-7; don't know where else a double bond could go.

[goiterjoe]

delta 9 is the plant version of THC, and there are numerous government patents on different variations of delta 8 THC.  I think that ferrous chloride would work in much the same way that phosphorous oxychloride would(as a proton donating lewis acid), but then again bad things have happened before because of me thinking.  ferrous chloride would be a hell of a lot easier to get than phosphorous oxychloride, since POCl3 is supposedly watched due to it's use in LSD(?) synthesis.

most patents using similar precursors report their highest yeilds being somewhere in the 30-40% range, so there probably would be several byproducts.  Shulgin mentioned that the reaction of pulegone and olivetol could result in up to 8 different active isomers of THC being created in the end product.

If pacman influenced us, we'd glide around dark rooms eating pills and listen to repetitive music.

[terbium]

delta 9 is the plant version of THC, and there are numerous government patents on different variations of delta 8 THC.

The numbering scheme that I am familar with does not allow for a delta-8 or delta-9. It is either delta-1 or delta-6 that is the principal form found in marijuana. Can you tell me where the pertinent double bond is in the delta-8 or delta-9 THC as numbered according to this new scheme? I am sort of surprised that there is this new numbering scheme since by my count there are only 7 positions where the double bond can go.

[eli3]

in the book "The Connoisseur's Handbook Of Marijuana"; they quote Scientific American(from December of 1969) as saying, "The delta-1 form is believed to be the active component...".

Oddly in up to date information i have always heard the reference be to delta-9.

"pull the wool over your own eyes"

[Rhodium]

Delta-1 is the same thing as Delta-9, just like Delta-3 is equivalent to Delta-8. It is just a different kind of numbering scheme, one using the older terpene nomenclature (Delta 8/9), and the other is the more recent IUPAC-ish nomenclature (Delta 1/3).

http://rhodium.lycaeum.org