Cannabinoids. 3. Synthetic approaches to 9-ketocannabinoids. Total synthesis of nabilone

Archer, Robert A.; Blanchard, W. B.; Day, W.A.; Johnson, Douglas W.; Lavagnino, E. R.; Ryan, Charles W.; Baldwin, Jack E.

doi:10.1021/jo00433a020

Cited by 81 publications

(56 citation statements)

References 3 publications

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“…Notably, Lilly's efforts had led to the synthesis and development of the drug Nabilone, 41 which has been used by patients receiving cancer chemotherapy. Also, companies such as Abbott and Arthur D. Little Inc. were developing nitrogen containing analogs (eg.…”

Section: Historymentioning

confidence: 99%

2012 Division of Medicinal Chemistry Award Address. Trekking the Cannabinoid Road: A Personal Perspective

Makriyannis

2014

J. Med. Chem.

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My involvement with the field of cannabinoids spans close to three decades, and covers a major part of my scientific career. It also reflects the robust progress in this initially largely unexplored area of biology. During this period of time, I have witnessed the growth of modern cannabinoid biology, starting from the discovery of its two receptors and followed by the characterization of its endogenous ligands and the identification of the enzyme systems involved in their biosynthesis and biotransformation. I was fortunate enough to start at the beginning of this new era and participate in a number of the new discoveries. It has been a very exciting journey. By covering some key aspects of my work during this period of “modern cannabinoid research,” this perspective, in part historical, intends to give an account of how the field grew, the key discoveries, and the most promising directions for the future.

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Section: Historymentioning

confidence: 99%

2012 Division of Medicinal Chemistry Award Address. Trekking the Cannabinoid Road: A Personal Perspective

Makriyannis

2014

J. Med. Chem.

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“…[144] However, Eli Lilly has also developed syntheses of the enantiomerically pure product, starting from β-pinene. [145,146] The alkylated resorcinol is obtained from tri-O-methyl pyrogallol by regioselective demethylation with borontrichloride, followed by a Friedel-Crafts alkylation with the appropriate tertiary alcohol. The demethylation is highly regio selective, because the central methoxy group sticks out of the plane of the benzene ring so that the oxygen is more basic than its neighbours.…”

Section: Nabilonementioning

confidence: 99%

Pharmaceuticals

Schaefer

2014

Natural Products in the Chemical Industry

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A boy who is born in Germany today has a probable life expectancy of around 77 years, and a girl one of 82 years -twice as long as in the year 1880. This increase is a consequence of both, better living circumstances -working conditions, food, clothing, housing -, and also a result of more comprehensive medical care. Thus, a whole range of infectious diseases has been wiped out, or brought at least under control, and the mortality rate for civilisation-and age-related diseases has dropped. Vaccinations and drugs play a key role in this outcome. The 20th century is characterised especially by the worldwide blossoming of the pharmaceutical industry. More and more, the targeted search for and development of new drugs have replaced serendipitous discoveries (Fig. 5.1). Pharmaceuticals of the last century.

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“…In spite of the fact that this synthesis was developed for the forming of ∆9-THC it also could be used for the synthesis of nabilone. A newer synthesis route is described by Archer et al [74]. The pentyl side chain homologous compound of nabilone, 11-nor-9-ketohexahydrocannabinol, is a useful precursor in the chemical synthesis of the major metabolites of ∆9-THC, e.g., 11-nor-9-carboxy-∆9-THC (THC-COOH) [75].…”

Section: Derivates Of 9-thcmentioning

confidence: 99%