Synthesis of a novel series of tetracyclic opioid antagonists incorporating an 8-aminobicyclo[3.2.1]oct-6-ene sub-unit

• Published in: Tetrahedron letters Vol. 44; no. 46; pp. 8411 - 8415
• Main Authors: Miller, J.A, Pope, S.A, Riddall, D.R, Ullah, G.M, Welsh, G.M
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 10.11.2003; Elsevier
• Subjects: [3+2]cycloaddition; alkynes; allyl cations; bicycle[3.2.1]oct-ene/-ane amines; Chemistry; Chemistry, Organic; dezocine; opioid antagonist; Physical Sciences; Science & Technology; μ receptors; [3+2]cycloaddition; opioid antagonist; allyl cations; alkynes; dezocine; bicycle[3.2.1]oct-ene/-ane amines; μ receptors; BRIDGED AMINOTETRALINS; AGONISTS; POTENT; OPIATE; mu receptors; STEREOSELECTIVE TOTAL SYNTHESIS; (3+2)CYCLOADDITION; YLANGO SESQUITERPENOIDS; ANALGESICS; RECEPTOR-BINDING
• ISSN: 0040-4039; 1873-3581
• DOI: 10.1016/j.tetlet.2003.09.104

The bridged bicyclo[3.2.1]oct-ene and -ane amines 9– 13 have been prepared via [3+2]cycloaddition of allylic alcohols 6 to alkynes 7 , and assessed as ligands at opioid receptors. Amine 10b is a potent antagonist at μ receptors. [3+2]Cycloaddition of allylic derivatives to alkynes is the key synthetic step in the preparation of opioid antagonist amines.