Communication
Organic & Biomolecular Chemistry
depending on the reagent will show utility in organic
synthesis.
79, 10734; (b) F. E. Michael, P. A. Sibbald and
B. M. Cochran, Org. Lett., 2008, 10, 793; (c) G. Broggini,
V. Barbera, E. M. Beccalli, E. Borsini, S. Galli, G. Lanza
and G. Zecchi, Adv. Synth. Catal., 2012, 354, 159;
(d) P. Szolcsányi and T. Gracza, Tetrahedron, 2006, 62,
8498; (e) G. Broggini, V. Barbera, E. M. Beccalli,
U. Chiacchio, A. Fasana, S. Galli and S. Gazzola, Adv.
Synth. Catal., 2013, 355, 1640.
5 K.-Y. Dong, H.-T. Qin, F. Liu and C. Zhu, Eur. J. Org. Chem.,
2015, 1419.
6 (a) G. Liu, W. Li and Y. Li, Adv. Synth. Catal., 2013, 355,
395; (b) G. Liu, Z. Ding, L. Zhang, T. Li, L. Li, L. Duan and
Y. Li, Adv. Synth. Catal., 2014, 356, 2303.
Acknowledgements
This work was financially supported by the National Natural
Science Foundation of China (Grant No. 21302134), the
Natural Science Foundation of Jiangsu (Grant No.
BK20130338) and the Priority Academic Program Development
of Jiangsu Higher Education Institutions (PAPD).
Notes and references
7 P. H. Fuller, J. Kim and S. R. Chemler, J. Am. Chem. Soc.,
2008, 130, 17638.
1 For selected recent examples of lactones with biological
activities, see: (a) Y. Pu, J.-H. Kang, D. M. Sigano,
M. L. Peach, N. E. Lewin, V. E. Marquez and
P. M. Blumberg, J. Med. Chem., 2014, 57, 3835;
(b) Q. Zhang, Y. Lu, Y. Ding, J. Zhai, Q. Ji, W. Ma, M. Yang,
H. Fan, J. Long, Z. Tong, Y. Shi, Y. Jia, B. Han, W. Zhang,
C. Qiu, X. Ma, Q. Li, Q. Shi, H. Zhang, D. Li, J. Zhang,
J. Lin, L.-Y. Li, Y. Gao and Y. Chen, J. Med. Chem., 2012, 55,
8757; (c) E. J. Salaski, G. Krishnamurthy, W.-D. Ding, K. Yu,
8 (a) M. T. Bovino and S. R. Chemler, Angew. Chem., Int. Ed.,
2012, 51, 3923; (b) E. S. Sherman, S. R. Chemler, T. B. Tan
and O. Gerlits, Org. Lett., 2004, 6, 1573; (c) E. S. Sherman,
P. H. Fuller, D. Kasi and S. R. Chemler, J. Org. Chem., 2007,
72, 3896.
9 (a) C.-L. Zhu, J.-S. Tian, Z.-Y. Gu, G.-W. Xing and H. Xu,
Chem. Sci., 2015, 6, 3044; (b) D.-F. Lu, G.-S. Liu, C.-L. Zhu,
B. Yuan and H. Xu, Org. Lett., 2014, 16, 2912.
S. S. Insaf, C. Eid, J. Shim, J. I. Levin, K. Tabei, L. Toral- 10 (a) T. Arunachalam, H. Fan, K. M. R. Pillai and
Barza, W.-G. Zhang, L. A. McDonald, E. Honores,
C. Hanna, A. Yamashita, B. Johnson, Z. Li, L. Laakso,
D. Powell and T. S. Mansour, J. Med. Chem., 2009, 52, 2181.
R. S. Ranganathan, J. Org. Chem., 1995, 60, 4428;
(b) M. Tiecco, L. Testaferri, M. Tingoli and F. Marini,
J. Chem. Soc., Chem. Commun., 1994, 221.
2 For selected examples of 5-membered lactams as pharma- 11 The crystal structure of 2a unambiguously confirmed that
ceutical agents, see: (a) G. Giannini, L. Vesci, G. Battistuzzi,
D. Vignola, F. M. Milazzo, M. B. Guglielmi, M. Barbarino,
this cyclization was oxybromination and the 1H NMR of
crude product showed no corresponding lactam generated.
M. Santaniello, N. Fanto, M. Mor, S. Rivara, D. Pala, 12 CCDC 1045561 (for 2a) and CCDC 1045560 (for 4d) contain
M. Taddei, C. Pisano and W. Cabri, J. Med. Chem., 2014, 57, the crystallographic data for this paper.
8358; (b) X. Wu, P. Ohrngren, A. A. Joshi, A. Trejos, 13 M. Newcomb, in Radicals in Organic Synthesis, ed.
M. Persson, R. K. Arvela, H. Wallberg, L. Vrang,
A. Rosenquist, B. B. Samuelsson, J. Unge and M. Larhed,
P. Renaud and M. P. Sibi, Wiley-VCH, Weinheim, Germany,
2001, vol. 1, pp. 317–336.
J. Med. Chem., 2012, 55, 2724; (c) H. M. Kim, D.-K. Ryu, 14 F. Liu, K. Liu, X. Yuan and C. Li, J. Org. Chem., 2007, 72,
Y. Choi, B. W. Park, K. Lee, S. B. Han, C.-W. Lee, 10231.
M.-R. Kang, J. S. Kang, S. K. Boovanahalli, S.-K. Park, 15 For selected recent examples of the Cu(III) intermediate
J. W. Han, T.-G. Chun, H.-Y. Lee, K.-Y. Nam, E. H. Choi and
G. Han, J. Med. Chem., 2007, 50, 2737.
3 For reviews on lactonization and lactamization, see:
(a) S. Robin and G. Rousseau, Tetrahedron, 1998, 54, 13681;
(b) S. Robin and G. Rousseau, Eur. J. Org. Chem., 2002,
3099.
involved in reductive elimination, see: (a) A. M. Suess,
M. Z. Ertem, C. J. Cramer and S. S. Stahl, J. Am. Chem. Soc.,
2013, 135, 9797; (b) A. Casitas, M. Canta, M. Sola,
M. Costas and X. Ribas, J. Am. Chem. Soc., 2011, 133,
19386; (c) A. E. King, L. M. Huffman, A. Casitas, M. Costas,
X. Ribas and S. S. Stahl, J. Am. Chem. Soc., 2010, 132,
12068; (d) A. E. King, T. C. Brunold and S. S. Stahl, J. Am.
Chem. Soc., 2009, 131, 5044.
4 For selected examples, see: (a) Z. Zhang, L. Ouyang,
W. Wu, J. Li, Z. Zhang and H. Jiang, J. Org. Chem., 2014,
Org. Biomol. Chem.
This journal is © The Royal Society of Chemistry 2015