Organic Letters
Letter
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magnesium-promoted one-pot deprotection−dehydration re-
action further allows rapid access to an advanced precursor and
facile cyclization to the indolactam tricycle. A key advantage of
our strategy is the application of our optimized copper-
catalyzed amino acid arylation, which provides a high yielding
method for introduction of diverse hydrophobic subunits. We
anticipate that application of this protocol to acidic, basic, and
unnatural amino acids will serve as a versatile platform for
diversification of the indolactam scaffold. Ongoing studies are
focused on the synthesis and biological evaluation these
analogues as well as more elaborate members of the indolactam
alkaloid family.
́
́
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10, 1371. (b) Irie, K.; Yanagita, R. C.; Torii, K.; Nakagawa, Y.
Heterocycles 2007, 73, 289.
ASSOCIATED CONTENT
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S
* Supporting Information
The Supporting Information is available free of charge on the
(13) (a) Nakagawa, Y. Biosci., Biotechnol., Biochem. 2012, 76, 1262.
(b) Irie, K.; Nakagawa, Y.; Ohigashi, H. Curr. Pharm. Des. 2004, 10,
1371.
(14) (a) Bogi, K.; Lorenzo, P.; Szallasi, Z.; Acs, P.; Wagner, G. S.;
̈
Experimental procedures and characterization of the
described compounds (PDF)
Blumber, P. M. Cancer Res. 1998, 58, 1423. (b) Yotti, L. P.; Chang, C.
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(15) (a) Irie, K.; Yanagita, R. C.; Nakagawa, Y. Med. Res. Rev. 2012,
32, 518. (b) Kedei, N.; Lubart, E.; Lewin, N. E.; Telek, A.; Lim, L.;
Mannan, P.; Garfield, S. H.; Kraft, M. B.; Keck, G. E.; Kolusheva, S.;
Jelinek, R.; Blumberg, P. M. ChemBioChem 2011, 12, 1242.
(16) Nakagawa, Y.; Irie, K.; Komiya, Y.; Ohigashi, H.; Tsuda, K.-I.
Tetrahedron 2004, 60, 7077.
AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
(17) (a) Kajiyama, S.-I.; Irie, K.; Kido, T.; Koshimizu, K.; Hayashi,
H.; Arai, M. Tetrahedron 1991, 47, 5453. (b) Hirota, M.; Suganuma,
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ACKNOWLEDGMENTS
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This study was supported by generous startup funds from the
San Francisco State University College of Science and
Engineering.
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