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Volumn 51, Issue 52, 2010, Pages 6806-6809

Decomplexation-nitroso Diels-Alder (NDA) approach to C,D-ring functionalisation for hippeastrine

Author keywords

Deprotection; Hippeastrine; Nitroso Diels Alder; Organoiron; Tandem reactions

Indexed keywords

ALKALOID; AROMATIC NITROSO COMPOUND; HIPPEASTRINE; POLYCYCLIC AROMATIC HYDROCARBON; UNCLASSIFIED DRUG;

EID: 78650676599     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2010.09.118     Document Type: Article
Times cited : (16)

References (93)
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    • A recent focus on catalytic enantioselective NDA reactions has increased the popularity of the method. See, for example
    • A recent focus on catalytic enantioselective NDA reactions has increased the popularity of the method. See, for example: (a) Jana, C. K.; Grimme, S.; Struder, A. Chem. Eur. J. 2009, 15, 9078-9084;
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    • For a review on asymmetric NDA reactions, see: Yamamoto, Y.; Yamamoto, H. Eur. J. Org. Chem. 2006, 9, 2031-2043.
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    • For other examples in target molecule synthesis, see: Sancibrao, P.; Karila, D.; Kouklovsky, C.; Vincent, G. J. Org. Chem. 2010, 75, 4333-4336 (porantheridine);
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    • For a classic example to control C-N bond formation in alkaloid synthesis, see: Iida, H.; Watanabe, Y.; Kibayashi, C. J. Org. Chem. 1985, 50, 1818-1825.
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    • The acylnitroso class of heterodienophiles does not naturally give this regioselectivity (see Ref. 13), but Shea's approach overcomes this difficulty by using an intramolecular cycloaddition strategy
    • The acylnitroso class of heterodienophiles does not naturally give this regioselectivity (see Ref. 13), but Shea's approach overcomes this difficulty by using an intramolecular cycloaddition strategy.
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    • Tandem decomplexation/NDA is important because ofthe sensitive (see Ref. 9) lactone ring in this diene ligand (see Fig. 1a)
    • Tandem decomplexation/NDA is important because ofthe sensitive (see Ref. 9) lactone ring in this diene ligand (see Fig. 1a).
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    • There has been considerable recent interest in applications of 2-nitrosopyridine reagents in MEND (Modular Enhancement of Nature's Diversity) procedures (Yang, B.; Zöllner, T.; Gebhard, P.; Möllmann, U.; Miller, M. J. Org. Biomol. Chem. 2010, 8, 691-697;
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    • including polymer-supported examples. This has provided many examples of high-yielding NDA reactions with this class of heterodienophile
    • including polymer-supported examples: Krchnak, V.; Möllmann, U.; Dahse, H.-M.; Miller, M.J. J. Comb. Chem. 2008, 10, 112-117. This has provided many examples of high-yielding NDA reactions with this class of heterodienophile.
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    • The reported regioselectivity may be a consequence of the Cu(I)-catalysis (see Refs. 14, 5a) which is not compatible with the use of trimethylamine N-oxide in the tandem decomplexation/NDA procedure
    • The reported regioselectivity may be a consequence of the Cu(I)-catalysis (see Refs. 14, 5a) which is not compatible with the use of trimethylamine N-oxide in the tandem decomplexation/NDA procedure.
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    • Møller's study (Ref. 17; 1996) also performed semiempirical AM1 calculations to identify the orientation of the aryl group. Our 2000 (Ref. 9) example and the two examples reported in this Letter show similar orientations of the aryl group in the solid state and support the earlier conclusions based on calculations. For a crystallographically defined pyridyl example, see Ref. 15. See also Ref. 25
    • Møller's study (Ref. 17; 1996) also performed semiempirical AM1 calculations to identify the orientation of the aryl group. Our 2000 (Ref. 9) example and the two examples reported in this Letter show similar orientations of the aryl group in the solid state and support the earlier conclusions based on calculations. For a crystallographically defined pyridyl example, see Ref. 15. See also Ref. 25.
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    • Attempts to nitrosylate the benzyl ether of phenol were unsuccessful, so we examined nitrobenzyl ether in the expectation that this would deactivate the benzyl arene and so improve selectivity for the phenyl ether ring
    • Attempts to nitrosylate the benzyl ether of phenol were unsuccessful, so we examined nitrobenzyl ether in the expectation that this would deactivate the benzyl arene and so improve selectivity for the phenyl ether ring.
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    • The corresponding nitrosylations of anisole and 4-nitrophenyl phenyl ether are known: Atherton, J. H.; Modie, R. B.; Noble, D. R.; O'Sulivan, B. J. Chem. Soc., Perkin Trans. 2 1997, 663-664; See also Ref. 19a.
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    • note
    • -1) in the gas phase].
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