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Volumn 62, Issue 6, 1997, Pages 1675-1686

Asymmetric construction of a quaternary carbon center by tandem [4 + 2]/[3 + 2] cycloaddition of a nitroalkene. The total synthesis of (-)-mesembrine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; MESEMBRINE; UNCLASSIFIED DRUG;

EID: 0030974560     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo970079z     Document Type: Article
Times cited : (112)

References (98)
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    • The use of chiral vinyl ethers in the cycloaddition of (E)-2- substituted and (E)-1,2-disubstituted 1-nitroalkenes is extrememly effective in providing enantiomerically enriched cycloadducts in good yield and with high diastereocontrol. For examples see footnotes 1 and 28 as well as: Denmark, S. E.; Marcin, L. R. J. Org. Chem. 1995, 60, 3221.
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    • For total syntheses of (+)-mesembrine see: (a) Yamada, S.; Otani, G. Tetrahedron Lett. 1971, 12, 1133. (b) Kosugi, H.; Miura, Y.; Kanna, H.; Uda, H. Tetrahedron Asymmetry 1993, 4, 1409. (c) Meyers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc. 1985, 107, 7776.
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    • For total syntheses of (+)-mesembrine see: (a) Yamada, S.; Otani, G. Tetrahedron Lett. 1971, 12, 1133. (b) Kosugi, H.; Miura, Y.; Kanna, H.; Uda, H. Tetrahedron Asymmetry 1993, 4, 1409. (c) Meyers, A. I.; Hanreich, R.; Wanner, K. T. J. Am. Chem. Soc. 1985, 107, 7776.
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    • For total syntheses of natural (-)-mesembrine see: (a) Strauss, H. F.; Weichers, A. Tetrahedron Lett. 1979, 20, 4495. (b) Takano, S.; Imamura, Y.; Ogasawara, K. Tetrahedron Lett. 1981, 22, 4479. (c) Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1990, 1239. (d) Yoshimitsu, T.; Ogasawara, K. Heterocycles 1996, 42, 135.
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    • For total syntheses of natural (-)-mesembrine see: (a) Strauss, H. F.; Weichers, A. Tetrahedron Lett. 1979, 20, 4495. (b) Takano, S.; Imamura, Y.; Ogasawara, K. Tetrahedron Lett. 1981, 22, 4479. (c) Takano, S.; Samizu, K.; Ogasawara, K. Chem. Lett. 1990, 1239. (d) Yoshimitsu, T.; Ogasawara, K. Heterocycles 1996, 42, 135.
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    • For the preparation of nitroalkene 2 see reference 13
    • For the preparation of nitroalkene 2 see reference 13.
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    • note
    • 2, methylaluminum(bis-2,6-diisopropylphenoxide) (MAIPh), and methyl aluminum bis(2,6-diphenylphenoxide) (MAPh) were found to be ineffective in promoting the desired cycloaddition.
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    • note
    • Isomerization can also be achieved using DMAP in methylene chloride. Starting from either the pure (Z)- or (E)-nitroalkene, a mixture of nitroalkenes isomers was recovered in approximately a 5/1 (E/Z) ratio in 53% yield. The rest of the material consisted of a mixture of nitroalkenes in which the olefin had isomerized away from the nitro substituent.
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    • note
    • (b) The TCC vinyl ether 16 has been found to undergo highly selective exo-mode [4 + 2] cycloadditions when using the aluminum-based Lewis acid MAPh.
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    • note
    • A racemic sample of the N-protected amine (±)-20 that was needed to establish chiral HPLC conditions was prepared from racemic vinyl ether (±)-16 using a parallel sequence of reactions.
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    • note
    • 2O) that followed the conversion of the starting aldehyde into a single product.
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    • note
    • A sample of the hydrochloride salt of natural mesembrine (∼7 mg) was kindly provided by Professor Steven A. Martin (University of Texas). Conversion of the hydrochloride salt back to the free amine was accomplished by passing a chloroform solution of the sample through a short plug of basic alumina (activity I).
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    • note
    • 13C NMR spectra of natural and synthetic mesembrine is included in the Supporting Information.
  • 94
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    • Unpublished results, University of Illinois, Urbana
    • Middleton, D. S. Unpublished results, University of Illinois, Urbana.
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  • 95
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    • The program Macromodel version 3.5a, Columbia University, was employed for these caculations
    • The program Macromodel version 3.5a, Columbia University, was employed for these caculations.
  • 96
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    • rel = 0.55 kcal/ mol) exhibited very little π-facial shielding
    • rel = 0.55 kcal/ mol) exhibited very little π-facial shielding.
  • 97
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    • The si- and re-faces of the enol ether are defined with respect to the C(1) alkoxy-bearing carbon atom
    • The si- and re-faces of the enol ether are defined with respect to the C(1) alkoxy-bearing carbon atom.
  • 98
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    • The re- and si-faces of the nitroalkene are defined at the β-carbon atom of the nitroalkene
    • The re- and si-faces of the nitroalkene are defined at the β-carbon atom of the nitroalkene.


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