Combined metalation-cross coupling strategies: A synthesis of schumanniophytine by a key biaryl O-carbamate remote anionic fries rearrangement

European Journal of Organic Chemistry

Volumn , Issue 9, 2008, Pages 1507-1509

  Macklin, Todd K ^a   Reed, Mark A ^b   Snieckus, Victor ^a  

^a QUEEN S UNIVERSITY   (Canada)

^b MERCK RESEARCH LABORATORIES   (United States)

Author keywords

C C coupling; Directed remote metalation; Metalation; Total synthesis

Indexed keywords

EID: 53849146742     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200701116     Document Type: Article

References (40)

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11. T. K. Macklin, PhD Thesis, Queen's University, Canada, 2007.
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18. Handling and purification of this material proved difficult and was an unpleasant odiferous experience.
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20. -1); the latter was only observed upon aqueous quench, which suggests the potential for trapping of the tetrahedral intermediate (see Supporting Information).
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37. See, inter alia: regiospecific arene metalation: T.-H. Nguyen, N. T. T. Chau, A.-S. Castanet, K. P. P. Nguyen, J. Mortier, J. Org. Chem. 2007, 72, 3419-3429;
38. regiocontrolled ferrocene metalation: D. Herault, K. Aelvoet, A. J. Blatch, A. Al-Majid, C. A. Smethurst, A. Whiting, J. Org. Chem. 2007, 72, 71-75;
39. regioselective heteroarene metalation: C. Berghian, E. Condamine, N. Ple, A. Turck, I. Silaghi-Dumitrescu, C. Maiereanu, M. Darabantu, Tetrahedron 2006, 62, 7339-7354;
40. anionic ortho-quinone methide generation: R. M. Jones, R. W. Van De Water, C. C. Lindsey, C. Hoarau, T. Ung, T. R. R. Pettus, J. Org. Chem. 2001, 66, 3435-3441.