10.1002/chem.201703316
Chemistry - A European Journal
COMMUNICATION
Scheme 4. Successive Ring Expansion reactions (SuRE). a Conditions A: i) To lactam 9 (1 equiv.), pyridine (6 equiv.) and DMAP (0.1 equiv.) in CH2Cl2 (7
mL/mmol of 12) add 10 (1.5 equiv.) in CH2Cl2 (3 mL/mmol of 12),18 h at 50 °C; ii) DBU (10 equiv.), CH2Cl2 (10 mL/mmol), RT, 18 h. b 4.5 equiv. of 10a used.
[1]
(a) E. M. Driggers, S. P. Hale, J. Lee, N. K. Terrett, Nat. Rev. Drug Discov.
2008, 7, 608; (b) E. Marsault, M. L. Peterson, J. Med. Chem. 2011, 54,
1961; (c) F. Giordanetto, J. Kihlberg J. Med. Chem. 2014, 57, 278; (d) A.
K. Yudin, Chem. Sci. 2015, 6, 30.
[13] See references 1 and 3, and: (a) R. H. Kohli, C. T. Walsh, M. D. Burkart,
Nature 2002, 418, 658; (b) J. Gavenonis, B. A. Sheneman, T. R. Siegert,
M. R. Eshelman, J. A. Kritzer, Nat. Chem. Biol. 2014, 10, 716; (c) E. A.
Villar, D. Beglov, S. Chennamadhavuni, J. A. Porco Jr, D. Kozakov, S.
Vajda, A. Whitty, Nat. Chem. Biol. 2014, 10, 723; (d) W. Xu, Y. H. Lau,
G. Fischer, Y. S. Tan, A. Chattopadhyay, M. de la Roche, M. Hyvönen,
C. Verma, D. R. Spring, L. S. Itzhaki, J. Am. Chem. Soc. 2017, 139, 2245.
[14] See references 6a, 10 and: (a) R. Wälchli, A. Guggisberg, M. Hesse,
Tetrahedron Lett. 1984, 21, 2205; (b) U. Kramer, A. Guggisberg, M.
Hesse, H. Schmid, Angew. Chem. Int. Ed. 1978, 17, 200; (c) M. M.
Shemyakin, V. K. Antonov, A. M. Shkrob, V. I. Shchelokov, Z. E.
Agadzhanyan, Tetrahedron 1965, 21, 3537; (d) G. I. Glover, Robert B.
Smith, H. Rapoport, J. Am. Chem. Soc. 1965, 87, 2003; (e) J. M.
Muchowski, Can. J. Chem. 1970, 48, 1946, (f) A. N. Chulin, I. L. Rodionov,
L. K. Baidakova, L. N. Rodionova, T. A. Balashova, V. T. Ivanov, J.
Peptide Sci. 2005, 11, 175; (g) V. N. Azev, A. N. Chulin, I. L. Rodionov
2014, 50, 145.
[2]
[3]
(a) S. Dawn, M. B. Dewald, D. Sobransingh, M. C. Paderes, A. C.
Wibowo, M. D. Smith, J. A. Krause, P. J. Pellechia, L. S. Shimizu, J. Am.
Chem. Soc. 2011, 133, 7025.
J. Montenegro, M. R. Ghadiri, J. R. Granja, Acc. Chem. Res. 2013, 46,
2955.
[4]
[5]
T. Ema, D. Tanida, T. Sakai, J. Am. Chem. Soc. 2007, 129, 10591.
(a) K. E. Griffiths, J. F. Stoddart, Pure Appl. Chem. 2008, 80, 485; (b) N.
H. Evans, P. D. Beer, Chem. Soc. Rev. 2014, 43, 4658; (c) M. Xue, Y.
Yang, X. Chi, X. Yan, F. Huang, Chem. Rev. 2015, 115, 7398.
(a) M. Hesse in Ring Enlargement in Organic Chemistry, Wiley-VCH,
Weinheim, 1991; (b) Practical Medicinal Chemistry with Macrocycles, E.
Marsault, M. L. Peterson Eds, Wiley, 2017.
[6]
[7]
[8]
(a) J. Fastrez, J. Phys. Chem. 1989, 93, 2635; (b) J. C. Collins, K. James,
Med. Chem. Commun. 2012, 3, 1489.
[15] Y. Liu, S. Shi, M. Achtenhagen, R. Liu, M. Szostak, Org. Lett. 2017, 19
1614.
For prominent macrocyclisation methods and review articles, see: (a) Z.
J. Gartner, B. N. Tse, R. Grubina, J. B. Doyon, T. M. Snyder, D. R. Liu,
Science 2004, 305, 1601; (b) A. Parenty, X. Moreau, and J.-M.
Campagne, Chem. Rev., 2006, 106, 911; (c) R. Hill, V. Rai, A. K. Yudin,
J. Am. Chem. Soc. 2010, 132, 2889; 130, 15611; (d) C. J. White, A. K.
Yudin, Nat. Chem. 2011, 3, 509; (e) A. Fürstner, Science 2013, 341,
1229713; (f) A. P. Treder, J. L. Hickey, M.-C. J. Tremblay, S. Zaretsky,
C. C. G. Scully, J. Mancuso, A. Doucet, A. K. Yudin, E. Marsault, Chem.
Eur. J. 2015, 21, 9249.
[16] (a) J. Chatterjee, C. Gilon, A. Hoffman, H. Kessler, Acc. Chem. Res.,
2008, 41, 1331; (b) J. Chatterjee, F. Rechenmacher, H. Kessler, Angew.
Chem. Int. Ed. 2013, 52, 254; (c) D. P. Slough, H. Yu, S. M. McHugh, Y.-
S. Lin, Phys. Chem. Chem. Phys. 2017, 19, 5377.
[17] CCDC 1559565 contains the supplementary crystallographic data for this
paper. These data can be obtained free of charge from The Cambridge
[18] Products 11l–u, generated from enantiopure amino acid derivatives,
retained high negative [α]D values, suggesting that little/no epimerisation
takes place during ring expansion (see Supporting Information).
[19] (a) S. B. Y. Shin, B. Yoo, L. J. Todaro, K. Kirshenbaum, J. Am. Chem.
Soc. 2007, 129, 3218; (b) A. M. Webster, S. L. Cobb, Tetrahedron Lett.
2017, 58, 1010.
[9]
(a) F. Kopp, C. F. Stratton, L. B. Akella, D. S. Tan, Nat. Chem. Bio. 2012,
8, 358; (b) R. A. Bauer, T. A. Wenderski, D. S. Tan, Nat. Chem. Bio. 2013,
9, 21. (c) J. E. Hall, J. V. Matlock, J. W. Ward, J. Clayden, Angew. Chem.
Int. Ed. 2016, 55, 11153; (d) Z.-L. Li, X.-H. Li, N. Wang, N.-Y. Yang, X.-
Y. Liu, Angew. Chem. Int. Ed. 2016 55, 15100.
[10] For a review, see; J. R. Donald, W. P. Unsworth, Chem. Eur. J. 2017, 23,
8780.
[20] For a related β-lactam expansion, see: A. Klapars, S. Parris, K. W.
Anderson, S. L. Buchwald, J. Am. Chem. Soc. 2004, 126, 3529.
[21] For related ring expansion processes leading to lactone products, see;
(a) E. J. Corey, D. J. Brunelle, K. C. Nicolaou, J. Am. Chem. Soc. 1977,
99, 7359; (b) J. E. Forsee, J. Aubé, J. Org. Chem. 1999, 64, 4381.
[22] I. B. Seiple, Z. Zhang, P. Jakubec, A. Langlois-Mercier, P. M. Wright, D.
T. Hog, K. Yabu, S. R. Allu, T. Fukuzaki, P. N. Carlsen, Y. Kitamura, X.
[11] C. Kitsiou, J. J. Hindes, P. I’Anson, P. Jackson, T. C. Wilson, E. K. Daly,
H. R. Felstead, P. Hearnshaw, W. P. Unsworth, Angew. Chem. Int. Ed.
2015, 54, 15794
[12] L. G. Baud, M. A. Manning, H. L. Arkless, T. C. Stephens, W. P. Unsworth,
Chem. Eur. J. 2017, 9, 2225.
This article is protected by copyright. All rights reserved.