Stereoselective Synthesis of Nonpsychotic Natural Cannabidiol and Its Unnatural/Terpenyl/Tail-Modified Analogues

Here, we report a three-step concise and stereoselective synthesis route to one of the most important phytocannabinoids, namely, (−)-cannabidiol (-CBD), from inexpensive and readily available starting material R-(+)-limonene. The synthesis involved the diastereoselective bifunctionalization of limon...

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Veröffentlicht in:	Journal of organic chemistry 2022-04, Vol.87 (7), p.4489-4498
Hauptverfasser:	Anand, Radhika, Cham, Pankaj Singh, Gannedi, Veeranjaneyulu, Sharma, Sumit, Kumar, Mukesh, Singh, Rohit, Vishwakarma, Ram A, Singh, Parvinder Pal
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Sprache:	eng
Schlagworte:	Cannabidiol
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container_title	Journal of organic chemistry
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creator	Anand, Radhika Cham, Pankaj Singh Gannedi, Veeranjaneyulu Sharma, Sumit Kumar, Mukesh Singh, Rohit Vishwakarma, Ram A Singh, Parvinder Pal
description	Here, we report a three-step concise and stereoselective synthesis route to one of the most important phytocannabinoids, namely, (−)-cannabidiol (-CBD), from inexpensive and readily available starting material R-(+)-limonene. The synthesis involved the diastereoselective bifunctionalization of limonene, followed by effective elimination leading to the generation of key chiral p-mentha-2,8-dien-1-ol. The chiral p-mentha-2,8-dien-1-ol on coupling with olivetol under silver catalysis provided regiospecific (−)-CBD, contrary to reported ones which gave a mixture. The newly developed approach was further extended to its structural analogues cannabidiorcin and other tail/terpenyl-modified analogues. Moreover, its opposite isomer (+)-cannabidiol was also successfully synthesized from S-(−)-limonene.
doi_str_mv	10.1021/acs.joc.1c02571
format	Article
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title	Stereoselective Synthesis of Nonpsychotic Natural Cannabidiol and Its Unnatural/Terpenyl/Tail-Modified Analogues
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