Methods are provided for the synthesis of olivetol, olivetol analogs, cannabidiol (CBD), CBD analogs, and other cannabinoids; one method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC ((?)-trans-?.sup.9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.

Methods are provided for the synthesis of olivetol, olivetol analogs, cannabidiol (CBD), CBD analogs, and other cannabinoids; one method employs phloroglucinol or a phloroglucinol analog as a starting material. The syntheses are stereospecific, efficient, selective, and cost-effective, with little or no potential for generation of THC ((?)-trans-?.sup.9-tetrahydro-cannabinol) or any other psychoactive side product. Telescoped syntheses are also provided, as are new cannabinoids, pharmaceutical formulations, and methods of use.

Disclosed herein are methods, processes and compositions for preparing a compound of formula 8: (8), and formula 18: (18). The methods and processes comprise performing a first allylic oxidation, a protection reaction, a second allylic oxidation, a reduction reaction, performing an acid-catalyzed coupling reaction, a methylation reaction and a deprotection reaction. Disclosed herein are methods, processes and compositions for enantioselectively preparing compounds of formulae 8 and 18. Also disclosed herein are compositions comprising compounds of formulae 8, 18 and/or intermediates and/or starting material thereof. ##STR00001##

Disclosed herein are methods, processes and compositions for preparing a compound of formula 8: (8), and formula 18: (18). The methods and processes comprise performing a first allylic oxidation, a protection reaction, a second allylic oxidation, a reduction reaction, performing an acid-catalyzed coupling reaction, a methylation reaction and a deprotection reaction. Disclosed herein are methods, processes and compositions for enantioselectively preparing compounds of formulae 8 and 18. Also disclosed herein are compositions comprising compounds of formulae 8, 18 and/or intermediates and/or starting material thereof. ##STR00001##

Disclosed herein are methods, processes and compositions for preparing a compound of formula 8: (8), and formula 18: (18). The methods and processes comprise performing a first allylic oxidation, a protection reaction, a second allylic oxidation, a reduction reaction, performing an acid-catalyzed coupling reaction, a methylation reaction and a deprotection reaction. Disclosed herein are methods, processes and compositions for enantioselectively preparing compounds of formulae 8 and 18. Also disclosed herein are compositions comprising compounds of formulae 8, 18 and/or intermediates and/or starting material thereof. ##STR00001##

A process for producing alkyl R-lactate from an initial compound comprising substructure (I)

##STR00001##

is provided. The process involves producing an intermediate comprising R,R- and S,S-lactide from the initial compound, wherein the initial compound is subjected to stereoisomerisation conditions; and reacting at least a portion of the intermediate with an alkyl alcohol to produce a product comprising alkyl R-lactate, wherein alkyl R-lactate is produced in the presence of an enzyme. Also provided are processes for the production of R-lactic acid, oligomeric R-lactic acid, R,R-lactide, poly-R-lactic acid and stereocomplex lactic acid.

A process for producing alkyl R-lactate from an initial compound comprising substructure (I)

##STR00001##

is provided. The process involves producing an intermediate comprising R,R- and S,S-lactide from the initial compound, wherein the initial compound is subjected to stereoisomerisation conditions; and reacting at least a portion of the intermediate with an alkyl alcohol to produce a product comprising alkyl R-lactate, wherein alkyl R-lactate is produced in the presence of an enzyme. Also provided are processes for the production of R-lactic acid, oligomeric R-lactic acid, R,R-lactide, poly-R-lactic acid and stereocomplex lactic acid.

A process for the preparation of optionally asymmetric acetal compounds includes reacting a compound containing a hydroxyl group with a vinylether compound in the presence of a zwitterionic catalyst including at least one basic nitrogen containing structural fragment and at least one sulfonic acid group in its structure, with the proviso that a molar ratio of the basic nitrogen to sulfonic acid is 1:1.

A process for the preparation of optionally asymmetric acetal compounds includes reacting a compound containing a hydroxyl group with a vinylether compound in the presence of a zwitterionic catalyst including at least one basic nitrogen containing structural fragment and at least one sulfonic acid group in its structure, with the proviso that a molar ratio of the basic nitrogen to sulfonic acid is 1:1.

A process for the preparation of optionally asymmetric acetal compounds includes reacting a compound containing a hydroxyl group with a vinylether compound in the presence of a zwitterionic catalyst including at least one basic nitrogen containing structural fragment and at least one sulfonic acid group in its structure, with the proviso that a molar ratio of the basic nitrogen to sulfonic acid is 1:1.