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Volumn 73, Issue 14, 2008, Pages 5566-5569

New and expeditious tandem sequence Aza-Michael/intramolecular nucleophilic substitution route to substituted γ-lactams: Synthesis of the tricyclic core of (±)-martinellines

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CHEMICAL REACTIONS;

EID: 48249109103     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702752w     Document Type: Article
Times cited : (80)

References (44)
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    • Synthesis of all starting materials. (a) For a-bromoacetamides 9, see: Nilsson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2000, 2, 1939-1942.
    • Synthesis of all starting materials. (a) For a-bromoacetamides 9, see: Nilsson, B. L.; Kiessling, L. L.; Raines, R. T. Org. Lett. 2000, 2, 1939-1942.
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    • For Michael acceptors 8, see: May, B. C. H.; Zorn, J. A.; Witkop, J.; Sherrill, J.; Wallace, A. C.; Legname, G.; Prusiner, S. B.; Cohen, F. E. J. Med. Chem. 2007, 50, 65-73.
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    • See Experimental Section for the general procedure for the preparation of γ-lactams 1.
    • See Experimental Section for the general procedure for the preparation of γ-lactams 1.
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    • For representative existing methods, see ref 5a
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    • For the first asymmetric total synthesis of, )-martinelline and the second total synthesis of, )-martinellic acid, see: e
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    • 4-mediated domino reaction of 2-(cyanomethyl)-3-oxo-N-arylbutanamides was published. See: (a) Zhang, Z.; Zhang, Q.; Yan, Z.; Liu, Q. J. Org. Chem. 2007, 72, 9808-9810.
    • 4-mediated domino reaction of 2-(cyanomethyl)-3-oxo-N-arylbutanamides was published. See: (a) Zhang, Z.; Zhang, Q.; Yan, Z.; Liu, Q. J. Org. Chem. 2007, 72, 9808-9810.


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