Organic Letters
Letter
Scheme 2. Proposed Mechanism of the Homocoupling
Adebajo, A. C.; Kumar, V.; Aladesanmi, A. J. Phytochemistry 1994, 36,
1073. (e) Knolker, H. J.; Reddy, K. R. Chem. Rev. 2002, 102, 4303.
(5) (a) Ito, C.; Katsuni, S.; Ohta, H.; Omura, M.; Kajiura, I.;
Furukawa, H. Chem. Pharm. Bull. 1997, 45, 48. (b) Li, W. S.;
McChesney, J. D.; El-Feraly, F. S. Phytochemistry 1991, 30, 343.
(c) Maneerat, W.; Ritthiwigrom, T.; Cheenpracha, S.; Promgool, T.;
Yossathera, K.; Deachathai, S.; Phakhodee, W.; Laphookhieo, S. J. Nat.
Prod. 2012, 75, 741.
ASSOCIATED CONTENT
* Supporting Information
Text, figures, tables, and a CIF file giving experimental
procedures, atropisomerization measurements, characterization
data, crystallographic data, and calculations. This material is
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(6) (a) Wu, T.-S.; Wang, M.-L.; Lai, J.-S.; Ito, C.; Furukawa, H.
Phytochemistry 1991, 30, 1052. (b) Ito, C.; Thoyama, Y.; Omura, M.;
Kajiura, I.; Furukawa, H. Chem. Pharm. Bull. 1993, 41, 2096. (c) Tasler,
S.; Bringmann, G. Chem. Rec. 2002, 2, 113.
(7) (a) Bringmann, G.; Ledermann, A.; Stahl, M.; Gulden, K.-P.
Tetrahedron 1995, 51, 9353. (b) Lin, G.-Q; Zhang, A.-M. Tetrahedron
2000, 56, 7163.
AUTHOR INFORMATION
Corresponding Author
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Notes
The authors declare no competing financial interest.
(8) Knolker, H.-J.; Goesmann, H.; Hofmann, C. Synlett 1996, 737.
(9) Moody, C. J.; Shah, P. J. Chem. Soc., Perkin Trans 1 1989, 2463.
(10) Botman, P. N. M.; Postma, M.; Fraanje, J.; Goubitz, K.; SChenk,
H.; van Maarseveen, J. H.; Hiemstra, H. Eur. J. Org. Chem. 2002, 1952.
(11) Lee, Y. E.; Cao, T.; Torruellas, C.; Kozlowski, M. C. J. Am.
Chem. Soc. 2014, 136, 6782.
ACKNOWLEDGMENTS
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We are grateful to the NIH (GM-087605) and the NSF
(CHE1213230) for financial support of this research. Partial
instrumentation support was provided by the NIH for MS
(1S10RR023444) and NMR (1S10RR022442) and by the NSF
for an X-ray diffractometer (CHE 0840438) and HTE facilities
(GOALI CHE-0848460). L.L. thanks the China Scholarship
Council (201306350101) for financial support. We thank
Young Eun Lee (UPenn) for assistance and Osvaldo Gutierrez
(UPenn) for computational aid and helpful suggestions.
(12) (a) Katsuki, T. Chem. Soc. Rev. 2004, 33, 437. (b) Cozzi, P. G.
Chem. Soc. Rev. 2004, 33, 410.
(13) For reviews on vanadium in organic synthesis, see: (a) Hirao, T.
Chem. Rev. 1997, 97, 2707. (b) Bolm, C. Coord. Chem. Rev. 2003, 237,
245. (c) Reddy, P. P.; Chu, C.-Y.; Hwang, D.-R.; Wang, S.-K.; Uang,
B.-J. Coord. Chem. Rev. 2003, 237, 257. (d) Hirao, T. Pure Appl. Chem.
2005, 77, 1539.
(14) (a) Dejmek, M. M.; Selke, R. Angew. Chem., Int. Ed. 1998, 37,
1540. (b) Rehder, D.; Santoni, G.; Licini, G. M.; Schulzke, C.; Meier,
B. Coord. Chem. Rev. 2003, 237, 53. (c) Li, H.; Da, C.-S.; Xiao, Y.-H.;
Li, X.; Su, Y.-N. J. Org. Chem. 2008, 73, 7398. (d) Chen, C.; Kao, J.;
Salunke, S. B.; Lin, Y. Org. Lett. 2011, 13, 26. (e) Gisch, N.; Balzarini,
J.; Meier, C. J. Med. Chem. 2007, 50, 1658.
(15) (a) Kozlowski, M. C.; Morgan, B. J.; Linton, E. C. Chem. Soc.
Rev. 2009, 38, 3193. (b) Irie, R.; Masutani, K.; Katsuki, T. Synlett 2000,
1433. (c) Guo, Q.-X.; Wu, Z.-J.; Luo, Z.-B.; Liu, Q.-Z.; Ye, J.-L.; Luo,
S.-W.; Cun, L.-F.; Gong, L.-Z. J. Am. Chem. Soc. 2007, 129, 13927.
(d) Takizawa, S.; Katayama, T.; Sasai, H. Chem. Commun. 2008, 4113.
(e) Podlesny, E. E.; Kozlowski, M. C. J. Org. Chem. 2013, 78, 466.
(f) Egami, H.; Katsuki, T. J. Am. Chem. Soc. 2009, 131, 6082. (g)
Egami, H.; Matsumoto, K.; Oguma, T.; Kunisu, T.; Katsuki, T. J. Am.
Chem. Soc. 2010, 132, 13633. Radosevich, A. T.; Musich, C.; Toste, F.
D. J. Am. Chem. Soc. 2005, 127, 1090.
REFERENCES
■
(1) (a) Kongkathip, N.; Kongkathip, B. Heterocycles 2009, 79, 121.
(b) Rahman, M. M.; Gray, A. I. Phytochemistry 2005, 66, 1602.
(c) Thongthoom, T.; Songsiang, U.; Phaosiri, C.; Yenjai, C. Arch.
Pharm. Res. 2010, 33, 675.
(2) (a) Ramsewak, R. S.; Nair, M. G.; Strasburg, G. M.; DeWitt, D.
L.; Nitiss, J. L. J. Agric. Food Chem. 1999, 47, 444. (b) Wang, Y. S.; He,
H. P.; Shen, M. Y.; Hong, X.; Hao, X. J. J. Nat. Prod. 2003, 66, 416.
(c) Ito, C.; Itoigawa, M.; Aizawa, K.; Yoshida, K.; Ruangrungsi, N.;
Furukawa, H. J. Nat. Prod. 2009, 72, 1202.
(3) (a) Potterat, O. Curr. Org. Chem. 1997, 1, 415. (b) Kato, S.;
Kawai, H.; Kawasaki, T.; Toda, Y.; Urata, T.; Hayakawa, Y. J. Antibiot.
1989, XLII, 1879. (c) Iwatsuki, M.; Niki, E.; Kato, S. BioFactors 1993,
4, 123. (d) Tanaka, M.; Shin-ya, K.; Furihata, K.; Seto, H. J. Antibiot.
1995, 48, 326. (e) Roy, M. K.; Thalang, V. N.; Trakoontivakorn, G.;
Nakahara, K. Biochem. Pharmacol. 2004, 67, 41.
(4) (a) Narasimhan, N. S.; Paradhar, M. V.; Chitguppi, V. P.
Tetrahedron Lett. 1968, 53, 5501. (b) Chowdhury, B. K.; Chakraborty,
D. P. Phytochemistry 1971, 10, 1967. (c) Bhattacharyya, L.; Roy, S. K.;
Chakraborty, D. P. Phytochemistry 1982, 21, 2432. (d) Reisch, J.;
(16) Walsh, P. W.; Kozlowski, M. C. Fundamentals of Asymmetric
Catalysis; University Science Books: Sausalito, CA, 2009.
D
Org. Lett. XXXX, XXX, XXX−XXX