4.4 Article

Efficient one-pot synthetic approaches for cannabinoid analogues and their application to biologically interesting (-)-hexahydrocannabinol and (+)-hexahydrocannabinol

Journal

TETRAHEDRON LETTERS
Volume 49, Issue 20, Pages 3283-3287

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tetlet.2008.03.075

Keywords

cannabinoid; ethylenediamine diacetate/triethylamine; hetero diels-alder reaction; (-)-hexahydrocannabinol; (+)-hexahydrocannabinol

Funding

  1. Korea Evaluation Institute of Industrial Technology (KEIT) [B0008557] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)
  2. National Research Foundation of Korea [과C6B1910] Funding Source: Korea Institute of Science & Technology Information (KISTI), National Science & Technology Information Service (NTIS)

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This Letter reports new and efficient synthetic approaches for biologically interesting cannabinoid analogues. The key strategies involve ethylenediamine diacetate/triethylalmine-catalyzed cyclization. As an application of this methodology, one-step synthesis of biologically active natural (-)-hexahydrocannabinol and its unnatural enantiomer (+)-hexahydrocannabinol was carried out. (c) 2008 Elsevier Ltd. All rights reserved.

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