Please do not adjust margins
Organic & Biomolecular Chemistry
Page 4 of 4
COMMUNICATION
Journal Name
X. Luo, J. S. Fossey, W. -P. Deng, DJ.OOI:r1g0..1C0h3Ve9im/eCw.9A2Ort0iBc10le40O2,n47li7n9Be,
1156-1165; (b) Y. Li, L. Cao, X. Luo, W. -P. Deng,
Tetrahedron. 2014, 70, 5974-5979; (c) Z. -L. Wang, X. -L.
An, L. -S. Ge, J. -H. Jin, X. Luo, W. -P. Deng, Tetrahedron,
2014, 70, 3788-3792.
has the advantages of readily available starting materials,
concise steps and mild conditions.
Conclusion
15 C. A. Morales-Rivera, P. E. Floreancig, P. Liu, J. Am.
Chem. Soc. 2017, 139, 17935-17944.
In summary, a novel method to synthesize dibenzo[b,d]
oxepin-7(6H)-one was developed via visible-light-induced
cascade reaction of etherification/C-C coupling cyclization
from ɑ-bromoacetophenones and phenols. Twenty five
desired products were obtained in moderate to good yields by
this method. Furthermore, this protocol was applied to the
synthesis of Protosappanin A. The protocol features are simple
reaction conditions, readily available starting materials, broad
substrate scope, and good tolerance of functional groups.
16 (a) M. Parasram, P. Chuentragool, D. Sarkar, V.
Gevorgyan, J. Am. Chem. Soc. 2016, 138, 6340-6343;
(b) M. Parasram, V. Gevorgyan, Chem. Soc. Rev. 2017,
46, 6227-6240; (c) M. Parasram, P. Chuentragool, Y.
Wang, Y. Shi, V. Gevorgyan, J. Am. Chem. Soc. 2017,
139, 14857-14860.
17 (a) S. Feng, T. Li, C. Du, P. Chen, D. Song, J. Li, X.
She, Chem. Commun. 2017, 53, 4585-4588; (b)Y. Zhao,
Y. Lv and W. Xia, Chem. Rec. 2018, 18, 1-17; (c) Y. Yuan,
W. Dong, X. Gao, H. Gao, X. Xie, Z. Zhang, J. Org.
Chem. 2018, 83, 2840-2846.
18 (a) C. Zhou, P. H. Li, X. J. Zhu, L. Wang, Org. Lett. 2015,
17, 6198-6201; (b) C. L. Wang, J. Y. Qiao, X. C. Liu, H.
Song, Z. Z. Sun, W. Y. Chu, J. Org. Chem. 2018, 83,
1422-1430.
Conflicts of interest
There are no conflicts to declare.
19 (a) L. Grande, E. Serrano, L. Cuesta, E. P. Urriolabeitia,
Organometallics, 2012, 31, 394-404; (b) M. -T. Chicote,
C. Rubio, D. Bautista, J. Vicente, Dalton Trans. 2014, 43,
15170-15182.
Acknowledgements
This study was funded by the Natural Science Foundation of
Heilongjiang Province of China (No. B2018012).
Notes and references
1
S. Strych and D. Trauner, Angew. Chem., Int. Ed. 2013,
52, 9509-9512.
(a) K. Ohmori, M. Tamiya, M. Kitamura, H. Kato, M.
Oorui and K. Suzuki, Angew. Chem., Int. Ed. 2005, 44,
3871-3874; (b) S. Strych, G. Journot, R. P. Pemberton, S.
C. Wang, D. J. Tantillo and D. Trauner, Angew. Chem.,
Int. Ed. 2015, 54, 5079-5083.
2
3
4
5
S. M. Hein, J. B. Gloer, B. Koster, J. Nat. Prod. 1998, 61,
1566-1567.
J. Kornsakulkarn, S. Saepua, P. Laksanacharoen,
Tetrahedron Lett. 2016, 57, 305-307.
S. Tewtrakul, P. Chaniad, S. Pianwanit, C. Karalai, C.
Ponglimanont and O. Yodsaoue, Phytother. Res. 2015,
29, 724-729.
(a)I. Batubara, T. Mitsunaga and H. Ohashi, J. Wood Sci.
2010, 56, 77-81; (b) B. S. Min, T. D. Cuong, T. M. Hung,
B. K. Min, B. S. Shin and M. H. Woo, Bioorg. Med. Chem.
Lett. 2012, 22, 7436-7439; (c) N. Masahiro, N. Seiji, L.
Shumei, E. Ikuyo and K. Kenichi, Biol. Pharm. Bull. 1986,
34, 1-6.
6
7
8
9
J. L. Wang, J.Q. Liu, H. Lan, W. Y. Chu, & Z. Z.
Sun, Synthesis, 2015, 47, 3049-3060.
J. Q. Liu, X. Zhou, C. L. Wang, W. Y. Fu, W. Y. Chu and Z.
Z. Sun, Chem. Commun. 2016, 52, 5152–5155.
(a) D. -S. Kim, W. -J. Park, C. -H. Jun, Chem. Rev. 2017,
117, 8977-9015; (b) Y. Yang, J. Lan, J. You, Chem. Rev.
2017, 117, 8787-8863; (c) J. He, M. Wasa, K. S. L. Chan,
Q. Shao, J. -Q. Yu, Chem. Rev. 2017, 117, 8754-8786.
10 X. Zhang, Z. Xu, W. Si, K. Oniwa, M. Bao, Y. Yamamoto, T.
Jin, Nat. Commun. 2017, 8, 15073.
11 N. G. Schmidt, E. Eger, W. Kroutil, ACS Catal. 2016, 6,
4286-4311.
12 P. Gandeepan, C. H. Hung, C. H. Cheng, Chem. Commun.
2012, 48, 9379-9381.
13 J. Wu, J. Lan, S. Guo, J. You, Org. Lett. 2014, 16, 5862-
6865.
4 | J. Name., 2012, 00, 1-3
This journal is © The Royal Society of Chemistry 20xx
Please do not adjust margins