Journal of the American Chemical Society
transformation. For example, substituted N-Boc-proline
Page 4 of 5
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8
methyl ester and highly substituted cyclohexyl fragments were
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and 44 in useful yields and in good d.r. (7:1 and > 20:1,
respectively). Additionally, adduct 45 was obtained from the
oxalate of pregnenolone, a naturally occurring steroid, further
emphasizing the potential of employing native functionality to
access new structural analogues or to perform late stage
functionalization.
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9
photoredox
aryl amination
73%
10
11
12
13
14
15
16
17
18
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20
21
22
23
24
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26
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60
OCF3
OH
4 steps
N
Boc
N
46
simple, commercially
available alcohol
photoredox
NC
alcohol coupling 56%
via:
N
OCF3
O
NH
Ir
Cl
N
Et
Ni
Q203
N
Qurient Therapeutics
drug candidate for the treatment of tuberculosis
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Figure 2. Synthesis of a Precursor to Q203 via Sequential
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excellent yield.
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ASSOCIATED CONTENT
Supporting Information
The Supporting Information is available free of charge on
the ACS Publications website at DOI: (link to DOI)
AUTHOR INFORMATION
Corresponding Author
*dmacmill@princeton.edu
Notes
The authors declare no competing financial interests.
(13) See Supporting Information for measurement details.
(14) Durandetti, M.; Devaud, M.; Périchon, J. New J. Chem. 1996,
20, 659.
ACKNOWLEDGMENT
(15) See Supporting Information for characterization data.
(16) Biswas, S.; Weix, D. J. J. Am. Chem. Soc. 2013, 135, 16192.
(17) Tang, J.; Wang, B.; Wu, T.; Wan, J.; Tu, Z.; Njire, M.; Wan, B.;
Franzblauc, S. G.; Zhang, T.; Lu, X.; Ding, K. ACS Med. Chem. Lett.
2015, 6, 814.
(18) Corcoran, E. B.; Pirnot, M. T.; Lin, S.; Dreher, S. D.; DiRocco,
D. A.; Davies, I. W.; Buchwald, S. L.; MacMillan, D. W. C. Science
2016, 353, 279.
Support was provided by NIH NIGMS R01 01 GM093213-
01. X. Z. is grateful for a postdoctoral fellowship from the
Shanghai Institute of Organic Chemistry. Patricia Zhang,
Tracy Liu, and Andrei Iosub are thanked for their help in
preparing this manuscript.
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