A compound represented by a formula (A),

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W is

##STR00002##

and T is H,

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and R.sup.1-R.sup.8 are defined as defined above.

The present invention relates to methods of making fused ring compounds, such as indeno-fused naphthols, and fused ring indenopyran compounds, such as indeno-fused naphthopyrans, that each employ an unsaturated compound represented by the following Formula II.

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Referring to the unsaturated compound of Formula II: Ring-A can be selected from optionally substituted aryl (e.g., phenyl); m can be, for example, from 0 to 4; R.sup.1 for each m can be selected from optionally substituted hydrocarbyl (e.g., C.sub.1-C.sub.6 alkyl) optionally interrupted with at least one linking group (e.g., O); and R.sup.3 and R.sup.16 can each be independently selected from, for example, hydrogen or optionally substituted hydrocarbyl, such as C.sub.1-C.sub.8 alkyl. When Ring-A is a phenyl group, the unsaturated compound represented by Formula II can be referred to as an unsaturated indanone acid/ester compound, or an indenone acid/ester compound (depending on whether R.sup.16 is hydrogen, or an optionally substituted hydrocarbyl group).

The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

The present disclosure relates to the preparation of a cannabidiol compound or a derivative thereof. The cannabidiol compound or derivatives thereof can be prepared by an acid-catalyzed reaction of a suitably selected and substituted di-halo-olivetol or derivative thereof with a suitably selected and substituted cyclic alkene to produce a dihalo-cannabidiol compound or derivative thereof. The dihalo-cannabidiol compound or derivative thereof can be produced in high yield, high stereospecificity, or both. It can then be converted under reducing conditions to a cannabidiol compound or derivatives thereof.

The present disclosure concerns a group of cannabinoid compounds defined by formulas (I) to (IV), wherein R.sub.1 is H or COOH, for the first time isolated and fully characterized in structure, absolute stereochemistry by the present applicant. Methods of isolation, characterization, stereoselective synthesis, biological activity, pharmaceutical composition and therapeutic applications of the present compounds as modulators of the cannabinoid CB1 receptor are also object of the disclosure. ##STR00001##

The present disclosure concerns a group of cannabinoid compounds defined by formulas (I) to (IV), wherein R.sub.1 is H or COOH, for the first time isolated and fully characterized in structure, absolute stereochemistry by the present applicant. Methods of isolation, characterization, stereoselective synthesis, biological activity, pharmaceutical composition and therapeutic applications of the present compounds as modulators of the cannabinoid CB1 receptor are also object of the disclosure. ##STR00001##