A Convenient Synthesis of 1-Bromo4,5-dimethoxy-7-methylnaphthalene, a Naphthol Derivative Useful for Construction of Naphthylisoquinoline Alkaloids

Journal of Organic Chemistry

Volumn 62, Issue 24, 1997, Pages 8586-8588

  Hoye, Thomas R ^a   Mi, Liang ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000131763     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9713262     Document Type: Article

References (16)

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4. Hoye, T. R.; Mi, L. Tetrahedron Lett. 1996, 37, 3097.
5. (a) Bringmann, G. In The Alkaloids; Brossi, A., Ed.; Academic Press: New York, 1986; Vol. 29, Chapter 3.
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7. (a) Bringmann, G.; Gotz, R.; Ketter, P. A.; Walter, R.; Henschel, P.; Schaffer, M.; Stablein, M.; Kelly, T. R.; Boyd, M. R. Heterocycles 1994, 39 (2), 503.
8. (b) Rizzacasa, M. A.; Sargent, M. V. Aust. J. Chem. 1987, 40, 1737.
9. (a) Hoye, T. R.; Chen, M.; Mi, L.; Priest, O. P. Tetrahedron Lett. 1994, 35, 8747.
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11. Hobbs, P. D.; Upender, V.; Liu, J.; Pollart, P. J.; Thomas, D. W.; Dawson, M. I. J. Chem. Soc., Chem. Commun. 1996, 923.
12. 1H NMR spectrum of the major α-isomer compared with the minor β-isomer. We presume that the 2-bromo-5-methoxyphenyl ring is differentially shielding those resonances in the dominant conformation about C(3)-C(4) in which the two methine protons are anti.
13. Mix, R. C.; Cain, M. H.; Bhatia, A. V. Tetrahedron Lett. 1995, 36, 6413.
14. On one occasion the ketone 15 was accompanied by some of its enol trifluoroacetate. This mixture in methylene chloride was stirred under a layer of aqueous NaOH at room temperature for 24 h to cleave the enol ester. During this treatment, smooth conversion of the entire sample to the naphthol 16 was observed, indicating that even mildly basic treatment is sufficient to eliminate sulfinate and promote the aromatization.
15. We have also investigated the synthesis of the O-MOM analogue 9b starting from 4-bromo-1-(methoxymethoxy)-3-methylbenzene by a route entirely analogous to that depicted in Scheme 2 for the anisole derivative. On one occasion it was equally successful, including the Friedel-Crafts cyclization of the O-MOM analogue of the 4-arylbutanoic acid 14α/β. However, that acid-catalyzed cyclization (TFAA) to produce the O-MOM analogue of the tetralines 15α/β has proven to be irreproducible.
16. Breslow, R.; Garratt, S.; Kaplan, L.; LaFollette, D. J. Am. Chem. Soc. 1968, 90, 4051.