Organic Letters
Letter
as a key intermediate for the synthesis of natural products and
promising electronic materials.
Jiang, H.; Portelli, V. J. Aust. J. Chem. 1990, 43, 1291−1295. (d) Ojida,
A.; Nonaka, H.; Miyahara, Y.; Tamaru, S.; Sada, K.; Hamachi, I. Angew.
Chem., Int. Ed. 2006, 45, 5518−5521. (e) Kogan, K.; Biali, S. E. Org.
Lett. 2007, 9, 2393−2396.
ASSOCIATED CONTENT
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6) (a) Ho
̈
lscher, D.; Schneider, B. Phytochemistry 2005, 66, 59−64.
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Supporting Information
(b) Julianti, E.; Lee, J.-H.; Liao, L.; Park, W.; Park, S.; Oh, D.-C.; Oh,
K.-B.; Shin, J. Org. Lett. 2013, 15, 1286−1289. (c) Rukachaisirikul, V.;
Rungsaiwattana, N.; Klaiklay, S.; Phongpaichit, S.; Borwornwiriyapan,
K.; Sakayaroj, J. J. Nat. Prod. 2014, 77, 2375−2382. (d) Intaraudom,
C.; Nitthithanasilp, S.; Rachtawee, P.; Boonruangprapa, T.; Prabpai, S.;
Kongsaeree, P.; Pittayakhajonwut, P. Phytochemistry 2015, 120, 19−27.
Experimental details, H and 13C NMR spectra of new
1
compounds, and COSY and NOESY spectra of 10H and
(e) Gao, S.-S.; Duan, A.; Xu, W.; Yu, P.; Hang, L.; Houk, K. N.; Tang,
Y. J. Am. Chem. Soc. 2016, 138, 4249−4259.
(7) (a) Mukherjee, A.; Sau, S. C.; Mandal, S. K. Acc. Chem. Res. 2017,
X-ray data for compound 22 (CIF)
5
(
0, 1679−1691. (b) Kubo, T. Chem. Rec. 2015, 15, 218−232.
c) Morita, Y.; Ohba, T.; Haneda, N.; Maki, S.; Kawai, J.; Hatanaka, K.;
Sato, K.; Shiomi, D.; Takui, T.; Nakasuji, K. J. Am. Chem. Soc. 2000,
22, 4825−4826. (d) Paira, R.; Singh, B.; Hota, P. K.; Ahmed, J.; Sau,
S. C.; Johnpeter, J. P.; Mandal, S. K. J. Org. Chem. 2016, 81, 2432−
441.
AUTHOR INFORMATION
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ORCID
Present Address
(9) Bacci, J. P.; Kearney, A. M.; Van Vranken, D. L. J. Org. Chem.
2
(
005, 70, 9051−9053.
10) Genaev, A. M.; Salnikov, G. E.; Shernyukov, A. V.; Zhu, Z.;
Koltunov, K. Y. Org. Lett. 2017, 19, 532−535.
(11) After confirming the formation of the intermediates in TFA,
methanesulfonic acid was superadded to the solution and heated to 50
∥
Graduate School of Natural Sciences, Nagoya City University.
Notes
°
C. The desired phenalenone 3 was afforded in 85% yield.
The authors declare no competing financial interest.
(12) Laundon, B.; Morrison, G. A. J. Chem. Soc. C 1971, 1694−1704.
ACKNOWLEDGMENTS
The authors are grateful to Prof. Hajime Iwamoto (Niigata
University) for useful suggestions for the synthesis of 8-bromo-
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-naphthol and Ms. Kyohko Ohmine (ICR, Kyoto University)
for the NMR measurements. This study was carried out using
the Fourier transform ion cyclotron resonance mass spec-
trometer and the NMR in the Joint Usage/Research Center at
the Institute for Chemical Research, Kyoto University. This
study was supported in part by KAKENHI (No. 15K14931)
and Grant-in-Aid from the Tokyo Biochemical Research
Foundation.
REFERENCES
1) (a) Masters, K. S.; Bras
b) Winter, D. K.; Sloman, D. L.; Porco, J. A., Jr. Nat. Prod. Rep. 2013,
■
(
̈
e, S. Chem. Rev. 2012, 112, 3717−3776.
(
3
0, 382−391. (c) Wei, X.; Liang, D.; Wang, Q.; Meng, X.; Li, Z. Org.
Biomol. Chem. 2016, 14, 8821−8831. (d) Tang, Y. X.; Fu, W. W.; Wu,
R.; Tan, H. S.; Shen, Z. W.; Xu, H. X. J. Nat. Prod. 2016, 79, 1752−
1761.
(
2) (a) Urano, Y.; Kamiya, M.; Kanda, K.; Ueno, T.; Hirose, K.;
Nagano, T. J. Am. Chem. Soc. 2005, 127, 4888−4894. (b) Yang, Y.;
Lowry, M.; Schowalter, C. M.; Fakayode, S. O.; Escobedo, J. O.; Xu,
X.; Zhang, H.; Jensen, T. J.; Fronczek, F. R.; Warner, I. M.; Strongin,
R. M. J. Am. Chem. Soc. 2006, 128, 14081−14092. (c) Kim, S. H.;
Gunther, J. R.; Katzenellenbogen, J. A. Org. Lett. 2008, 10, 4931−4934.
(
(
d) Li, J.; Hu, M.; Yao, S. Q. Org. Lett. 2009, 11, 3008−3011.
e) Katori, A.; Azuma, E.; Ishimura, H.; Kuramochi, K.; Tsubaki, K. J.
Org. Chem. 2015, 80, 4603−4610. (f) Yamagami, A.; Ishimura, H.;
Katori, A.; Kuramochi, K.; Tsubaki, K. Org. Biomol. Chem. 2016, 14,
1
0963−10972.
3) Azuma, E.; Kuramochi, K.; Tsubaki, K. Tetrahedron 2013, 69,
694−1699.
4) (a) Vandana, T.; Prasad, K. J. R. Indian J. Chem., Sect. B 2005, 44,
15−818. (b) Mottram, L. F.; Maddox, E.; Schwab, M.; Beaufils, F.;
Peterson, B. R. Org. Lett. 2007, 9, 3741−3744.
5) (a) Bichan, D. J.; Yates, P. Can. J. Chem. 1975, 53, 2054−2063.
b) Sundholm, E. G. Tetrahedron 1978, 34, 577−586. (c) Elix, J. A.;
(
1
(
8
(
(
D
Org. Lett. XXXX, XXX, XXX−XXX