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C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines

Author(s)
Loach, Richard Peter; Fenton, Owen S.; Amaike, Kazuma; Siegel, Dustin Scott; Ozkal, Erhan; Movassaghi, Mohammad; ... Show more Show less
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Abstract
A versatile strategy for C7-selective boronation of tryptophans, tryptamines, and 3-alkylindoles by way of a single-pot C2/C7-diboronation–C2-protodeboronation sequence is described. The combination of a mild iridium-catalyzed C2/C7-diboronation followed by an in situ palladium-catalyzed C2-protodeboronation allows efficient entry to valuable C7-boroindoles that enable further C7-derivatization. The versatility of the chemistry is highlighted by the gram-scale synthesis of C7-boronated N-Boc-L-tryptophan methyl ester and the rapid synthesis of C7-halo, C7-hydroxy, and C7-aryl tryptophan derivatives.
Date issued
2014-10
URI
http://hdl.handle.net/1721.1/109780
Department
Massachusetts Institute of Technology. Department of Chemistry
Journal
Journal of Organic Chemistry
Publisher
American Chemical Society (ACS)
Citation
Loach, Richard P.; Fenton, Owen S.; Amaike, Kazuma; Siegel, Dustin S.; Ozkal, Erhan and Movassaghi, Mohammad. "C7-Derivatization of C3-Alkylindoles Including Tryptophans and Tryptamines." 79, no. 22 (November 2014): 11254–11263 © 2014 American Chemical Society
Version: Final published version
ISSN
0022-3263
1520-6904

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