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Volumn 44, Issue 4, 2005, Pages 606-609

Short, enantioselective total synthesis of stephacidin A

Author keywords

Alkaloids; Cascade reactions; Indoles; Natural products; Total synthesis

Indexed keywords

ESTERS; SYNTHESIS (CHEMICAL);

EID: 13244291528     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200461864     Document Type: Article
Times cited : (150)

References (46)
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    • For studies towards the total synthesis of the stephacidins or avrainvillamide, see: A. G. Myers, S. B. Herzon, J. Am. Chem. Soc. 2003, 125, 12080-12081; L. A. Adams, C. R. Gray, R. M. Williams, Tetrahedron Lett. 2004, 45, 4489-4493.
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    • For studies towards the total synthesis of the stephacidins or avrainvillamide, see: A. G. Myers, S. B. Herzon, J. Am. Chem. Soc. 2003, 125, 12080-12081; L. A. Adams, C. R. Gray, R. M. Williams, Tetrahedron Lett. 2004, 45, 4489-4493.
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    • Proline 13 was synthesized by hydroboration and protection (TBSCl) of the corresponding enantiopure allylated proline: D. Seebach, M. Boes, R. Naef, W B. Schweizer, J. Am. Chem. Soc. 1983, 105, 5390-5398;
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    • for further details, see Supporting Information
    • Proline 13 was synthesized by hydroboration and protection (TBSCl) of the corresponding enantiopure allylated proline: D. Seebach, M. Boes, R. Naef, W B. Schweizer, J. Am. Chem. Soc. 1983, 105, 5390-5398; M. G. Hinds, J. H. Welsh, D. M. Brennand, J. Fischer, M. J. Glennie, N. G. J. Richards, D. L. Turner, J. A. Robinson, J. Med. Chem. 1991, 34, 1777-1789; for further details, see Supporting Information.
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    • note
    • CCDC-248573 (23) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge via www.ccdc.cam.ac.uk/ retrieving.html (or from the Cambridge Crystallographic Data Centre, 12, Union Road, Cambridge CB21EZ, UK; fax; (+44)1223-336-033; or deposit@ccdc.cam. ac.uk).
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    • note
    • Detailed experimental procedures, copies of spectral data and full characterization are contained in the Supporting Information.


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