Organic Letters
Letter
Barrett, A. G. M. Tetrahedron Lett. 2005, 46, 6537. (h) Hilt, G.; Hess, W.;
Schmidt, F. Eur. J. Org. Chem. 2005, 2005, 2526. (i) Kraus, G. A.;
Hoover, K.; Zhang, N. Tetrahedron Lett. 2002, 43, 5319. (j) Seganish, W.
M.; DeShong, P. Org. Lett. 2006, 8, 3951. (k) Kim, Y. H.; Lee, H.; Kim,
Y. J.; Kim, B. T.; Heo, J.-N. J. Org. Chem. 2008, 73, 495.
to the formal synthesis of the biologically interesting alkaloid
( )-tylophorine.
ASSOCIATED CONTENT
* Supporting Information
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S
(10) (a) Furstner, A.; Mamane, V. J. Org. Chem. 2002, 67, 6264.
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The Supporting Information is available free of charge on the
(b) Mamane, V.; Hannen, P.; Furstner, A. Chem. - Eur. J. 2004, 10, 4556.
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(c) Mandal, A. B.; Lee, G.-H.; Liu, Y.-H.; Peng, S.-M.; Leung, M.-K. J.
Org. Chem. 2000, 65, 332. (d) Yao, T.; Campo, M. A.; Larock, R. C. Org.
Lett. 2004, 6, 2677. (e) Yao, T.; Campo, M. A.; Larock, R. C. J. Org.
Chem. 2005, 70, 3511.
Detailed experimental procedures, characterization data,
1
and copies of the H and 13C NMR spectra for all
previously unknown products (PDF)
̌ ́ ́
(11) (a) Pena, D.; Perez, D.; Guitian, E.; Castedo, L. J. Am. Chem. Soc.
1999, 121, 5827. (b) Kanno, K.-I.; Liu, Y.; Iesato, A.; Nakajima, K.;
Takahashi, T. Org. Lett. 2005, 7, 5453. (c) Liu, Z.; Larock, R. C. Angew.
Chem., Int. Ed. 2007, 46, 2535. (d) Yoshikawa, E.; Yamamoto, Y. Angew.
AUTHOR INFORMATION
Corresponding Authors
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Chem., Int. Ed. 2000, 39, 173. (e) Pen
Castedo, L. Eur. J. Org. Chem. 2003, 2003, 1238.
̌ ́ ́
a, D.; Perez, D.; Guitian, E.;
Notes
(12) (a) Himeshima, Y.; Sonoda, T.; Kobayashi, H. Chem. Lett. 1983,
1211. (b) Bronner, S. M.; Bahnck, K. B.; Garg, N. K. Org. Lett. 2009, 11,
1007. (c) Goetz, A. E.; Garg, N. K. Nat. Chem. 2012, 5, 54.
The authors declare no competing financial interest.
(13) For reviews of aryne chemistry, see: (a) Pellissier, H.; Santelli, M.
Tetrahedron 2003, 59, 701. (b) Wenk, H. H.; Winkler, M.; Sander, W.
Angew. Chem., Int. Ed. 2003, 42, 502. (c) Sanz, R. Org. Prep. Proced. Int.
2008, 40, 215. (d) Pena, D.; Perez, D.; Guitian, E. Angew. Chem., Int. Ed.
2006, 45, 3579. (e) Yoshida, H.; Ohshita, J.; Kunai, A. Bull. Chem. Soc.
Jpn. 2010, 83, 199. (f) Worlikar, S. A.; Larock, R. C. Curr. Org. Chem.
2011, 15, 3214. (g) Bhunia, A.; Yetra, S. R.; Biju, A. T. Chem. Soc. Rev.
2012, 41, 3140. (h) Gampe, C. M.; Carreira, E. M. Angew. Chem., Int. Ed.
2012, 51, 3766. (i) Tadross, P. M.; Stoltz, B. M. Chem. Rev. 2012, 112,
3550. (j) Wu, C.-R.; Shi, F. Asian J. Org. Chem. 2013, 2, 116.
(k) Dubrovskiy, A. V.; Markina, N. A.; Larock, R. C. Org. Biomol. Chem.
2013, 11, 191. (l) Perez, D.; Pena, D.; Guitian, E. Eur. J. Org. Chem.
2013, 2013, 5981. For reviews of heterocyclic arynes, see: (m) Goetz, A.
E.; Shah, T. K.; Garg, N. K. Chem. Commun. 2015, 51, 34. (n) Goetz, A.
E.; Garg, N. K. J. Org. Chem. 2014, 79, 846.
(14) (a) Worlikar, S. A.; Larock, R. C. Org. Lett. 2009, 11, 2413.
(b) Worlikar, S. A.; Larock, R. C. J. Org. Chem. 2009, 74, 9132.
(15) For recent syntheses of tylophorines, see: (a) McIver, A.; Young,
D. D.; Deiters, A. Chem. Commun. 2008, 4750. (b) Yamashita, S.;
Kurono, N.; Senboku, H.; Tokuda, M.; Orito, K. Eur. J. Org. Chem. 2009,
2009, 1173. (c) Niphakis, M. J.; Georg, G. I. Org. Lett. 2011, 13, 196.
(d) Xu, X.; Liu, Y.; Park, C.-M. Angew. Chem., Int. Ed. 2012, 51, 9372.
(e) Lahm, G.; Stoye, A.; Opatz, T. J. Org. Chem. 2012, 77, 6620. (f) Lin,
Q.-X.; Ho, T.-K. Tetrahedron 2013, 69, 2996. (g) Chuang, T.-H.; Lee, S.-
J.; Yang, C.-W.; Wu, P.-L. Org. Biomol. Chem. 2006, 4, 860.
ACKNOWLEDGMENTS
We thank Shaanxi University of Science and Technology for
financial support of this research (BJ15-33).
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