Organic Letters
Letter
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of stereogenic centers = 3.6 [0.25], AlogP = 2.76 [3.99], Glob
= 0.14 [0.08].33 To quantify the structural diversity of the
compound set, a Tanimoto similarity matrix was also generated
for all compounds (Figure S4), with a small average Tanimoto
coefficient of 0.19 (with 1.00 indicating identical structures).34
In addition, ≥25 mg were synthesized for most derivatives, and
compounds were produced at ≥95% purity. Collections of
compounds derived from natural products, such as those
disclosed herein, are structurally distinct from, but comple-
mentary to, existing screening libraries and will be useful for a
variety of biological investigations.
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ASSOCIATED CONTENT
* Supporting Information
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S
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(13) Evanno, L.; Lachkar, D.; Lamali, A.; Boufridi, A.; Seon-Meniel,
B.; Tintillier, F.; Saulnier, D.; Denis, S.; Genta-Jouve, G.; Jullian, J.-C.;
Leblanc, K.; Beniddir, M. A.; Petek, S.; Debitus, C.; Poupon, E. Eur. J.
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The Supporting Information is available free of charge on the
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J. D.; Spring, D. R. Bioorg. Med. Chem. 2017, 25, 2825−2843.
Experimental procedures, NMR spectra, and graphs of
physicochemical properties of all products (PDF)
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(b) Charaschanya, M.; Aube, J. Nat. Commun. 2018, 9, 934.
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Accession Codes
6−14.
(15) (a) Ibbeson, B. M.; Laraia, L.; Alza, E.; O’Connor, C. J.; Tan, Y.
S.; Davies, H. M. L.; McKenzie, G.; Venkitaraman, A. R.; Spring, D. R.
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CCDC 1853000 contains the supplementary crystallographic
data for this paper. These data can be obtained free of charge
bridge Crystallographic Data Centre, 12 Union Road,
Cambridge CB2 1EZ, UK; fax: +44 1223 336033.
(16) Richter, M. F.; Drown, B. S.; Riley, A. P.; Garcia, A.; Shirai, T.;
Svec, R. L.; Hergenrother, P. J. Nature 2017, 545, 299−304.
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AUTHOR INFORMATION
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Corresponding Author
ORCID
(18) Reviews of recent reports of biological activity: (a) Kornienko,
A.; Evidente, A. Chem. Rev. 2008, 108, 1982−2014. (b) Cao, Z. F.;
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Notes
The authors declare the following competing financial
interest(s): The University of Illinois has filed patents on
some of this work.
(19) Gerrard, A. W. Pharm. J. 1877, 8, 214.
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J.; Kornienko, A.; Kiss, R.; Evidente, A.; Pottier, L. Mini-Rev. Med.
Chem. 2010, 10, 41−50.
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(b) Toriizuka, Y.; Kinoshita, E.; Kogure, N.; Kitajima, M.; Ishiyama,
ACKNOWLEDGMENTS
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We thank Bryon Drown (UIUC) for assistance in computa-
tional analysis and Danielle Gray (UIUC) for collection and
analysis of X-ray data. Funding was provided by the NIH
(R01-GM118575) and the University of Illinois. S.Z.T. is an
HHMI Fellow of the Damon Runyon Cancer Research
Foundation (DRG-2776-16), and A.E.C. was supported by
an ACS DOC Summer Undergraduate Research Fellowship.
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A.; Otoguro, K.; Yamada, H.; Omura, S.; Takayama, H. Bioorg. Med.
Chem. 2008, 16, 10182−10189. (c) Tan, C.-X.; Schrader, K. K.;
Mizuno, C. S.; Rimando, A. M. J. Agric. Food Chem. 2011, 59, 5977−
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