Synthesis of morphine fragments spiro[benzofuran-3(2H),4'-piperidine] and octahydro-1H-benzofuro[3,2-e]isoquinoline by intramolecular heck reaction

Tetrahedron Letters

Volumn 38, Issue 26, 1997, Pages 4571-4574

  Cheng, Chen Yu ^a   Liou, Jing Ping ^a   Lee, Mei Jing ^a  

^a NATIONAL TAIWAN UNIVERSITY   (Taiwan)

Author keywords

[No Author keywords available]

Indexed keywords

MORPHINE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; DRUG SYNTHESIS; ISOMERISM;

EID: 0031004433     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(97)00976-3     Document Type: Article

References (22)

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8. The compatibility of radical cyclization and intramolecular Heck reaction has been reported. For examples, see: Kuehne, M. E.; Wang, T.; Seaton, P. J. J. Org. Chem. 1996, 61, 6001-6008; Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662.
9. The compatibility of radical cyclization and intramolecular Heck reaction has been reported. For examples, see: Kuehne, M. E.; Wang, T.; Seaton, P. J. J. Org. Chem. 1996, 61, 6001-6008; Mohanakrishnan, A. K.; Srinivasan, P. C. Tetrahedron Lett. 1996, 37, 2659-2662.
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13. 13C signals appear as pairs.)
14. For a review, see: Overman, L. E. Pure & Appl. Chem. 1994, 66, 1423-1430.
15. A 3-alkyl substituent has been shown to impart interesting conformational effects and morphine (μ) antagonism activity to 4-phenylpiperidine (AN) opioid compounds. See: Zimmerman, D. M.; Nickander, R.; Horng, J. S.; Wong, D. T. Nature 1978, 279, 332-334; Zimmerman, D. M.; Leander, J. D.; Cantrell, B. E.; Reel, J. K.; Snoddy, J.; Mendelsohn, L. G.; Johnson, B. G.; Mitch, C. H. J. Med. Chem. 1993, 36, 2834-2841.
16. A 3-alkyl substituent has been shown to impart interesting conformational effects and morphine (μ) antagonism activity to 4-phenylpiperidine (AN) opioid compounds. See: Zimmerman, D. M.; Nickander, R.; Horng, J. S.; Wong, D. T. Nature 1978, 279, 332-334; Zimmerman, D. M.; Leander, J. D.; Cantrell, B. E.; Reel, J. K.; Snoddy, J.; Mendelsohn, L. G.; Johnson, B. G.; Mitch, C. H. J. Med. Chem. 1993, 36, 2834-2841.
17. Compound 14 has been found to maintain weak binding affinity towards the μ opioid receptor (Ki, μ = 1,654 nM).
18. BINAP = 2,2′-bis(diphenylphosphano)-1,1′-binaphthyl: Noyori, R; Takaya, H. Acc. Chem. Res. 1990, 23, 345-350.
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20. For recent reviews, see: Shibasaki, M.; Sodeoka, M. J. Syn. Org. Chem., Japan 1994, 52, 956-67 (English); Schmalz, H. G. Nachr. Chem. Tech. Lab. 1994, 42, 270-276; Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.
21. For recent reviews, see: Shibasaki, M.; Sodeoka, M. J. Syn. Org. Chem., Japan 1994, 52, 956-67 (English); Schmalz, H. G. Nachr. Chem. Tech. Lab. 1994, 42, 270-276; Cabri, W.; Candiani, I. Acc. Chem. Res. 1995, 28, 2-7.
22. The e.e. was determined by HPLC analysis: ChiralCel OD; hexane/isopropanol = 9:1; UV: 254 nm; flow rate: 0.8 mL/min. The absolute configuration of (-)-12 was assigned based on analogy with (+)-15, which was synthesized in 49-55% e.e. under similar reaction conditions with (R)-(+)-BINAP. See: Ashimori, A.; Overman, L. E. J. Org. Chem. 1992, 57,4571-4572.