Kinetically controlled 'H/'H exchange at carbon atom 5 of (-)-1.6-dehydrosparteinium monoperchlorate ua) followed by sodium borohydride or sodium borodeuteride reduction of the iminium double bond gave optically active 5,5-('H,)-sparteine 0 and 5.5,6-('Hs)sparteine (16). respectively. Under thermody
Synthesis of nona-deutero olivetol and nona-deutero cannabinoids
✍ Scribed by Herbert H. Seltzman; Mosammat K. Begum; Christopher D. Wyrick
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- French
- Weight
- 387 KB
- Volume
- 29
- Category
- Article
- ISSN
- 0022-2135
No coin nor oath required. For personal study only.
✦ Synopsis
Abstract
Copper (I) catalyzed Grignard cross coupling of alkyl bromides provided a facile synthesis of d~9~‐olivetol [5‐(2,2,3,3,4,4,5,5,5‐^2^H~9~)pentyl‐1,3‐benzenediol] with high d~9~ incorporation levels and no detectable levels of d~0~ to d~7~ ions. The outcome of the coupling is dependent on which bromide is used as the Grignard reagent. d~9~‐Δ^9^‐THC and racemic d~9~‐11‐hydroxy‐Δ^9^‐THC suitable for GC/MS analysis were prepared from the olivetol.
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## Abstract Intramolecular electrophilic cyclization reactions were performed with 1‐(3‐oxo‐3‐phenylpropyl)‐1,2,5,6‐tetrahydropyridine derivatives 1a–p in strong acids to give 4,6‐diphenylsubstituted 1‐azabicyclo[3.3.1]nonadienes 2a–p. Some qualitative observations were made on substituents and rea