Novel rearrangement reaction of a 6,14-endoethanomorphinan derivative to a benzomorphan derivative

[1]  H. Nagase,et al.  Synthesis of a new opioid ligand having the oxabicyclo[3.2.1]octane skeleton using a new rearrangement reaction. , 2009, Bioorganic & medicinal chemistry letters.

[2]  S. Hirono,et al.  Synthesis of a stable iminium salt and propellane derivatives. , 2008, The Journal of organic chemistry.

[3]  Xiaobao Yang,et al.  Enantiocontrolled synthesis of (-)-9-epi-pentazocine and (-)-aphanorphine. , 2008, Organic letters.

[4]  M. Narita,et al.  Rational drug design and synthesis of a selective opioid receptor antagonist on the basis of the accessory site concept. , 2004, Bioorganic & medicinal chemistry letters.

[5]  M. Narita,et al.  Drug design and synthesis of epsilon opioid receptor agonist: 17-(cyclopropylmethyl)-4,5alpha-epoxy-3,6beta-dihydroxy-6,14-endoethenomorphinan-7alpha-(N-methyl-N-phenethyl)carboxamide (TAN-821) inducing antinociception mediated by putative epsilon opioid receptor. , 2004, Bioorganic & medicinal chemistry.

[6]  B. Trost,et al.  Migratory hydroamination: a facile enantioselective synthesis of benzomorphans. , 2003, Journal of the American Chemical Society.

[7]  W. Boulanger Improved Resolution of (±)-cis-2′-Hydroxy-5,9-dimethyl-6, 7-benzomorphan and Preparation of Racemic, (+)-, and (-)-cis-2-Methylcyclopropyl-2′-hydroxy-5,9-dimethyl-6,7-benzomorphan (Cyclazocine) , 1999 .

[8]  J. Fujimoto,et al.  Involvement of supraspinal epsilon and mu opioid receptors in inhibition of the tail-flick response induced by etorphine in the mouse. , 1992, The Journal of pharmacology and experimental therapeutics.

[9]  F. Carroll,et al.  An improved resolution of (±)-cis-N-normetazocine , 1990 .

[10]  P. Portoghese,et al.  The facility of formation of a .DELTA.6 bond in dihydromorphinone and related opiates , 1989 .

[11]  W. Stigelman,et al.  Goodman and Gilman's the Pharmacological Basis of Therapeutics , 1986 .

[12]  A. Meyers,et al.  Asymmetric synthesis of 2-alkyl pyrrolidines and piperidines. Synthesis of (+)-metazocine , 1985 .

[13]  H. Seto,et al.  Studies on the syntheses of heterocyclic compounds. 726. Thermal rearrangement of aminomethyl cyclopropyl ketones and a novel synthesis of pentazocine. , 1977, The Journal of organic chemistry.

[14]  T. Kametani,et al.  A novel cleavage of aryl benzyl ethers and allyl aryl ethers by sodium bis(2-methoxyethoxy)aluminum hydride. An alternative synthesis of pentazocine. , 1976, The Journal of organic chemistry.

[15]  T. Kametani,et al.  Studies on the syntheses of analgesics. XLVI. An abnormal Hofmann degradation of N-(4-hydroxybenzyl)-3-benzazocinium halides (studies on the syntheses of heterocyclic compounds. DCLXVIII). , 1976, Chemical & pharmaceutical bulletin.

[16]  K. Rice,et al.  Optical resolution of (+/-)-2,5-dimethyl-2'-hydroxy-9alpha- and -9beta-propyl-6,7-benzomorphans and their pharmacological properties. , 1976, Journal of medicinal chemistry.

[17]  T. Honda,et al.  Studies on the Syntheses of Heterocyclic Compounds. Part DCXXXVI. An Alternative Synthesis of Pentazocine , 1975 .

[18]  T. Kametani,et al.  Studies on the syntheses of heterocyclic compounds. DCXXVI. A modified synthesis of pentazocine. , 1975, Chemical & pharmaceutical bulletin.

[19]  K. W. Bentley,et al.  Novel analgesics and molecular rearrangements in the morphine-thebaine group. IV. Acid-catalyzed rearrangements of alcohols of the 6,14-endo-ethenotetrahydrothebaine series. , 1967, Journal of the American Chemical Society.

[20]  R. A. Hardy,et al.  Novel analgesics and molecular rearrangements in the morphine-thebaine group. V. Derivatives of 7,8-dihydrocyclohexeno[1',2':8,14]codeinone. , 1967, Journal of the American Chemical Society.

[21]  L. Harris,et al.  Benzomorphans. Optically Active and trans Isomers. , 1967, Journal of medicinal chemistry.

[22]  L. Harris,et al.  PENTAZOCINE. STRONG ANALGESICS AND ANALGESIC ANTAGONISTS IN THE BENZOMORPHAN SERIES. , 1964, Journal of medicinal chemistry.

[23]  E. C. Clarke Identification of Phenazocine, a Potent New Analgesic , 1959, Nature.

[24]  K. W. Bentley,et al.  Acid-Catalyzed Rearrangements in the Nepenthone Series , 1958 .

[25]  H. Nagase,et al.  A NOVEL ABNORMAL REARRANGEMENT IN THE FISCHER INDOLE SYNTHESIS , 1997 .

[26]  R. Noyori,et al.  General asymmetric synthesis of isoquinoline alkaloids. Enantioselective hydrogenation of enamides catalyzed by BINAP-Ruthenium(II) complexes , 1994 .

[27]  R. Noyori,et al.  General asymmetric synthesis of benzomorphans and morphinans via enantioselective hydrogenation , 1987 .

[28]  G. Morton,et al.  Novel analgesics and molecular rearrangements in the morphine--thebaine group. X. Further acid-catalysed rearrangements of alcohols in the 6,14-endo-ethenotetrahydroghebaine series. , 1969, Journal of the Chemical Society. Perkin transactions 1.

[29]  J. Lewis,et al.  Novel analgesics and molecular rearrangements in the morphine–thebaine group. Part VIII. 7-Alkyl-6,14-endo-ethenotetrahydrothebaine and related compounds , 1969 .

[30]  J. Bower,et al.  Novel analgesics and molecular rearrangements in the morphine-thebaine group. XVI. Some derivatives of 6,14-endo-etheno-7, 8-dihydromorphine. , 1969, Journal of the Chemical Society. Perkin transactions 1.