Organic Letters
Letter
(3) (a) Liu, H.; Yang, Y.; Wang, S.; Wu, J.; Wang, X.-N.; Chang, J.
Org. Lett. 2015, 17, 4472. (b) Chen, L.; Yu, L.; Deng, Y.; Zheng, Z.-J.;
Xu, Z.; Cao, J.; Xu, L.-W. Adv. Synth. Catal. 2016, 358, 480. (c) Chen,
L.; Cui, Y.-M.; Xu, Z.; Cao, J.; Zheng, Z.-J.; Xu, L.-W. Chem. Commun.
(14) (a) Zhang, Y.; Hsung, R. P.; Tracey, M. R.; Kurtz, K. C. M.;
Vera, E. L. Org. Lett. 2004, 6, 1151. (b) Zhang, X.; Zhang, Y.; Huang,
J.; Hsung, R. P.; Kurtz, K. C. M.; Oppenheimer, J.; Petersen, M. E.;
Sagamanova, I. K.; Shen, L.; Tracey, M. R. J. Org. Chem. 2006, 71,
4170. (c) Sagamanova, I. K.; Kurtz, K. C. M.; Hsung, R. P. Org. Synth.
2007, 84, 359.
(15) With increasing catalyst loading, reaction temperature, and/or
reaction time, the gradual conversion of 3p and 4f to 3p′ and 4f′,
respectively, was observed by TLC, suggesting that the formation of
3p′ and 4f′ is triggered by the initial generation of 3p and 4f.
However, initial loss of the OTBS group in ynamide 2s followed by
the Zn-catalyzed reaction of 1a/1n with the so-obtained ynamide
cannot be completely excluded.
̈
2016, 52, 11131. (d) Wezeman, T.; Zhong, S.; Nieger, M.; Brase, S.
Angew. Chem., Int. Ed. 2016, 55, 3823. (e) Han, P.; Mao, Z.-Y.; Si, C.-
M.; Zhou, Z.; Wei, B.-G.; Lin, G.-Q. J. Org. Chem. 2019, 84, 914.
(4) (a) Mulder, J. A.; Hsung, R. P.; Frederick, M. O.; Tracey, M. R.;
Zificsak, C. A. Org. Lett. 2002, 4, 1383. (b) Frederick, M. O.; Hsung,
R. P.; Lambeth, R. H.; Mulder, J. A.; Tracey, M. R. Org. Lett. 2003, 5,
2663.
(5) (a) Tanaka, R.; Hirano, S.; Urabe, H.; Sato, F. Org. Lett. 2003, 5,
67. (b) Kurtz, K. C. M.; Hsung, R. P.; Zhang, Y. Org. Lett. 2006, 8,
231. (c) You, L.; Al-Rashid, Z. F.; Figueroa, R.; Ghosh, S. K.; Li, G.;
Lu, T.; Hsung, R. P. Synlett 2007, 2007, 1656. (d) Saito, N.;
Katayama, T.; Sato, Y. Org. Lett. 2008, 10, 3829. (e) Saito, N.;
Katayama, T.; Sato, Y. Heterocycles 2010, 82, 1181. (f) Cook, A. M.;
Wolf, C. Chem. Commun. 2014, 50, 3151. (g) Yabuuchi, Y.;
Kuzuguchi, T.; Yoshimura, T.; Matsuo, J.-i. Org. Lett. 2016, 18, 4951.
(6) Grimster, N. P.; Wilton, D. A. A.; Chan, L. K. M.; Godfrey, C. R.
A.; Green, C.; Owen, D. R.; Gaunt, M. J. Tetrahedron 2010, 66, 6429.
(7) For examples on the spontaneous hydrolysis of an amide moiety
to give lactones but no recycling of amide byproducts, see: Li, L.; Zhu,
X.-Q.; Zhang, Y.-Q.; Bu, H.-Z.; Yuan, P.; Chen, J.; Su, J.; Deng, X.; Ye,
L.-W. Chem. Sci. 2019, 10, 3123. and ref 3c
(8) (a) Yu, L.; Cao, J. Org. Biomol. Chem. 2014, 12, 3986. Cu-
catalyzed three-component domino process of sulfonyl azide, alkyne,
and salicylaldehyde involving a ketenimine intermediate: (b) Mandal,
P. K. RSC Adv. 2014, 4, 5803. (c) Murugavel, G.; Punniyamurthy, T.
Org. Lett. 2013, 15, 3828. (d) Qian, W.; Amegadzie, A.;
Winternheimer, D.; Allen, J. Org. Lett. 2013, 15, 2986. (e) Cui, S.
L.; Lin, X. F.; Wang, Y. G. Org. Lett. 2006, 8, 4517.
(9) (a) Coumarins: Biology, Applications and Mode of Action;
O’Kennedy, R., Thornes, R. D., Eds.; John Wiley & Sons: Chichester,
1997. (b) Angle, S. R.; Rainier, J. D.; Woytowicz, C. J. Org. Chem.
1997, 62, 5884. (c) Van De Water, R. W.; Pettus, T. R. R. Tetrahedron
2002, 58, 5367. (d) Rosenau, T.; Potthast, A.; Elder, T.; Kosma, P.
Org. Lett. 2002, 4, 4285. (e) Uchiumi, F.; Hatano, T.; Ito, H.;
Yoshida, T.; Tanuma, S. Antiviral Res. 2003, 58, 89. (f) Piazzi, L.;
Rampa, A.; Bisi, A.; Gobbi, S.; Belluti, F.; Cavalli, A.; Bartolini, M.;
Andrisano, V.; Valenti, P.; Recanatini, M. J. Med. Chem. 2003, 46,
2279. (g) Santana, L.; Uriarte, E.; Roleira, F.; Milhazes, N.; Borges, F.
Curr. Med. Chem. 2004, 11, 3239. (h) Aggarwal, B. B.; Bhardwaj, A.;
Aggarwal, R. S.; Seeram, N. P.; Shishodia, S.; Takada, Y. Anticancer
Res. 2004, 24, 2783. (i) Borges, F.; Roleira, F.; Milhazes, N.; Santana,
L.; Uriarte, E. Curr. Med. Chem. 2005, 12, 887. (j) Rajendran, M.;
Inbaraj, J. J.; Gandhidasan, R.; Murugesan, R. J. Photochem. Photobiol.,
A 2006, 182, 67. (k) Magadula, J. J.; Erasto, P. Nat. Prod. Rep. 2009,
́
́
26, 1535. (l) Matos, M. J.; Teran, C.; Perez-Castillo, Y.; Uriarte, E.;
Santana, L.; Vina, D. J. Med. Chem. 2011, 54, 7127. (m) Zhao, H. P.;
̃
Yan, B.; Peterson, L. B.; Blagg, B. S. J. ACS Med. Chem. Lett. 2012, 3,
327.
(10) Mandal, P. S.; Kumar, A. V. Synlett 2016, 27, 1408 and
references therein .
(11) Selected recent examples: (a) Silvestri, R. Med. Res. Rev. 2009,
29, 295. (b) Cheng, Y.; Judd, T. C.; Bartberger, M. D.; Brown, J.;
Chen, K.; Fremeau, R. T.; Hickman, D.; Hitchcock, S. A.; Jordan, B.;
Li, V.; Lopez, P.; Louie, S. W.; Luo, Y.; Michelsen, K.; Nixey, T.;
Powers, T. S.; Rattan, C.; Sickmier, E. A.; St. Jean, D. J.; Wahl, R. C.;
Wen, P. H.; Wood, S. J. Med. Chem. 2011, 54, 5836. (c) Cinelli, M.
́
A.; Li, H.; Chreifi, G.; Martasek, P.; Roman, L. J.; Poulos, T. L.;
Silverman, R. B. J. Med. Chem. 2014, 57, 1513. (d) Holden, J. K.;
Lewis, M. C.; Cinelli, M. A.; Abdullatif, Z.; Pensa, A. V.; Silverman, R.
B.; Poulos, T. L. Biochemistry 2016, 55, 5587. (e) Cinelli, M. A.; Li,
H.; Chreifi, G.; Poulos, T. L.; Silverman, R. B. J. Med. Chem. 2017, 60,
3958.
(12) Youn, S. W.; Pastine, S. J.; Sames, D. Org. Lett. 2004, 6, 581.
(13) Lee, J.-W.; List, B. J. Am. Chem. Soc. 2012, 134, 18245.
E
Org. Lett. XXXX, XXX, XXX−XXX