The present invention describes a method which outlines a process for conversion of CBD to a Δ.sup.9-tetrahydrocannabinol (Δ.sup.9-THC) compound or derivative thereof involving treating a naturally produced CBD intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the Δ.sup.9-tetrahydrocannabinol compound or derivative thereof at a relatively high concentration. The source of the CBD is from industrial hemp having less than 0.3% Δ.sup.9-THC and extracting and purifying a CBD distillate or isolate or a combination thereof. This procedure will produce Δ.sup.9-THC that is essentially free from any other cannabinoids other than some trace amounts of the initial CBD starting material, or about 95% Δ.sup.9-THC and 2-4% CBD. Another aspect of the present invention relates to a process for further purification and enrichment of the Δ.sup.9-THC using distillation and collecting an essentially pure fraction of Δ.sup.9-THC using additional distillation or enrichment form of purification. Included are methods and processes to scale the reaction from the lab to large scale manufacturing. Included are methods for adding a molecule marker to authenticate high purity Δ.sup.9-THC products. Formulations and uses for pharmaceuticals, nutraceuticals, food products, and topicals are also provided.

The present invention describes a method which outlines a process for conversion of CBD to a Δ.sup.9-tetrahydrocannabinol (Δ.sup.9-THC) compound or derivative thereof involving treating a naturally produced CBD intermediate compound with an organoaluminum-based Lewis acid catalyst, under conditions effective to produce the Δ.sup.9-tetrahydrocannabinol compound or derivative thereof at a relatively high concentration. The source of the CBD is from industrial hemp having less than 0.3% Δ.sup.9-THC and extracting and purifying a CBD distillate or isolate or a combination thereof. This procedure will produce Δ.sup.9-THC that is essentially free from any other cannabinoids other than some trace amounts of the initial CBD starting material, or about 95% Δ.sup.9-THC and 2-4% CBD. Another aspect of the present invention relates to a process for further purification and enrichment of the Δ.sup.9-THC using distillation and collecting an essentially pure fraction of Δ.sup.9-THC using additional distillation or enrichment form of purification. Included are methods and processes to scale the reaction from the lab to large scale manufacturing. Included are methods for adding a molecule marker to authenticate high purity Δ.sup.9-THC products. Formulations and uses for pharmaceuticals, nutraceuticals, food products, and topicals are also provided.

Various aspects of this disclosure relate to gas phase methods to decarboxylate cannabinoid carboxylic acids.

Various aspects of this disclosure relate to gas phase methods to decarboxylate cannabinoid carboxylic acids.

The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ.sup.8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. ##STR00001##
Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed. ##STR00002##

The present invention relates to intermediate compounds for the synthesis of novel cannabinoids 1 and 2, synthesized from simple starting materials using a cascade sequence of allylic rearrangement, aromatization and, for tetracyclic cannabinoids, further highly stereoselective and regioselective cyclization. These synthesized cannabinoids can more easily be obtained at high purity levels than cannabinoids isolated or synthesized via known methods. The cannabinoids 2 are obtained containing very low levels of isomeric cannabinoids such as the undesirable Δ.sup.8-tetrahydrocannabinol. The analogues with variation in aromatic ring substituents, whilst easily synthesized with the new methodology, would be much more difficult to make from any of the components of cannabis oil. ##STR00001##
Novel compounds of the formulas 3 and 6, useful as intermediates for the synthesis of the cannabinoids of advanced intermediates 4 and 5 as well as cannabinoids of the formulas 1 and 2, are disclosed. ##STR00002##

There is disclosed a compound Formula I ##STR00001##
In Formula I: Z is CR.sup.4R.sup.5, C═CR.sup.4R.sup.5, SiR.sup.4R.sup.5, GeR.sup.4R.sup.5, NR.sup.4a, PR.sup.4a, P(O)R.sup.4a, O, S, SO, SO.sub.2, Se; SeO, SeO.sub.2, Te, TeO, or TeO.sub.2; R.sup.1-R.sup.3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, where two groups selected from R.sup.1, R.sup.2, and R.sup.3 can be joined together to form a fused ring; R.sup.4-R.sup.5 are the same or different at each occurrence and are H, D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl; R.sup.4ais alkyl, silyl, germyl, aryl, or a deuterated analog thereof; a is an integer from 0-4; b and c are the same or different and are an integer from 0-3.

There is disclosed a compound Formula I ##STR00001##
In Formula I: Z is CR.sup.4R.sup.5, C═CR.sup.4R.sup.5, SiR.sup.4R.sup.5, GeR.sup.4R.sup.5, NR.sup.4a, PR.sup.4a, P(O)R.sup.4a, O, S, SO, SO.sub.2, Se; SeO, SeO.sub.2, Te, TeO, or TeO.sub.2; R.sup.1-R.sup.3 are the same or different at each occurrence and are D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl, where two groups selected from R.sup.1, R.sup.2, and R.sup.3 can be joined together to form a fused ring; R.sup.4-R.sup.5 are the same or different at each occurrence and are H, D, aryl, heteroaryl, alkyl, amino, silyl, germyl, deuterated aryl, deuterated heteroaryl, deuterated alkyl, deuterated amino, deuterated silyl, or deuterated germyl; R.sup.4ais alkyl, silyl, germyl, aryl, or a deuterated analog thereof; a is an integer from 0-4; b and c are the same or different and are an integer from 0-3.

A compound represented by the following formula (1):

##STR00001## wherein each X independently represents an oxygen atom or a sulfur atom, or non-crosslinking, R.sup.1 represents a single bond or a 2n-valent group having 1 to 30 carbon atoms, the group may have an alicyclic hydrocarbon group, a double bond, a hetero atom, or an aryl group having 6 to 30 carbon atoms, each R.sup.2 independently represents a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a hydroxyl group, in which at least one R.sup.2 represents an alkoxy group having 1 to 30 carbon atoms or an aryloxy group having 6 to 30 carbon atoms, each m is independently an integer of 1 to 6, each p is independently 0 or 1, and n is an integer of 1 to 4.

A compound represented by the following formula (1):

##STR00001## wherein each X independently represents an oxygen atom or a sulfur atom, or non-crosslinking, R.sup.1 represents a single bond or a 2n-valent group having 1 to 30 carbon atoms, the group may have an alicyclic hydrocarbon group, a double bond, a hetero atom, or an aryl group having 6 to 30 carbon atoms, each R.sup.2 independently represents a straight, branched or cyclic alkyl group having 1 to 10 carbon atoms, an aryl group having 6 to 10 carbon atoms, an alkenyl group having 2 to 10 carbon atoms, an alkoxy group having 1 to 30 carbon atoms, an aryloxy group having 6 to 30 carbon atoms, or a hydroxyl group, in which at least one R.sup.2 represents an alkoxy group having 1 to 30 carbon atoms or an aryloxy group having 6 to 30 carbon atoms, each m is independently an integer of 1 to 6, each p is independently 0 or 1, and n is an integer of 1 to 4.