SYNTHESIS OF AN ISOMER OF TETRAHYDROCANNABINOL,
Abstract
Structure of tetrahydrocannabinol derived from natural sources is known except for the position of the isolated alicyclic double bond and the configuration about the 6 0d 10a-carbon atoms. The final resolution of the structure of natural tetrahydrocannabinol depends on the synthesis of the several possible isomers. An attempt to find a method for the preparation of the two pairs of diastereomeric cis- and trans-1-hydroxy-3-n-amyl 6, 6, 9-trimethyl-6a, 7, 10, 10a-tetrahydro-6 dibenzopyrans by a Diels-Alder condensation of isoprene with an appropriately substituted cou marin is reported. Results of the condensation of isoprene with 3-carboxycoumarin, 3-acetylcoumarin, 3-carboxy-5-hydroxy-7-amylcoumarin, and 3-carboxy 5-hydroxy-6-carbethoxy-7-amylcoumarin and the pre paration of trans-1-hydroxy-3-n-amyl-6, 6, 9 trimethyl-6a,7,10,10a-tetrahydro-6-dibenzopyran are described. Trans-1-hydroxy-3-n-amyl-6,6,9 trimethyl-6a,7,10,10a-tetrahydro-6-dibenzopyran is not identical with a tetrahydrocannabinol iso lated from hashish. Work is in progress on the synthesis and optical resolution of the cis- and trans-1-hydroxy-3-n-amyl-6,6,9-trimethyl-6a,7,10, 10a-tetrahydro-6-dibenzopyrans. (Author)
Document Details
- Document Type
- Technical Report
- Publication Date
- Mar 01, 1963
- Accession Number
- AD0411385
Entities
People
- F.w. Hoffmann
- Richard L. Hively
- Roger Steele
Organizations
- Edgewood Chemical Biological Center