Journal of the American Chemical Society
Page 4 of 5
ACKNOWLEDGMENT
1
We are grateful for financial support from National Institute
of Health (Grant GM-61591). We thank Dr. Binfeng Sun for
his early contribution to this project and Prof. Christine
Thomas’s group for the use of the IR spectrometer.
2
3
4
5
6
7
8
REFERENCES
(1) (a) Casteel, D. A. Nat. Prod. Rep. 1992, 9, 289. (b) Casteel, D. A.
Nat. Prod. Rep. 1999, 16, 55. (c) Liu, D.-Z.; Liu, J.-K. Nat. Prod. Bio-
prospect. 2013, 3, 161.
(2) For reviews of peroxy natural products as anticancer agents,
see: (a) Jung, M.; Kim, H.; Lee, K.; Park, M. Mini. Rev. Med. Chem.
2003, 3, 159. (b) Dembitsky, V. M.; Gloriozova, T. A.; Poroikov, V. V.
Mini. Rev. Med. Chem. 2007, 7, 571. (c) Dembitsky, V. M. Eur. J. Med.
Chem. 2008, 43, 223.
(3) For multiple steps syntheses of β-peroxy carboxylates from
chiral precursors, see: (a) Dussault, P. H.; Woller, K. R. J. Am. Chem.
Soc. 1997, 119, 3824. (b) Dussault, P. H.; Eary, C. T.; Woller, K. R. J.
Org. Chem. 1999, 64, 1789. (c) Dai, P.; Trullinger, T. K.; Liu, X.;
Dussault, P. H. J. Org. Chem. 2006, 71, 2283.
(4) For chiral auxiliary-assisted syntheses of β-peroxy carbox-
ylates, see: (a) Dussault, P. H.; Woller, K. R.; Hillier, M. C. Tetrahe-
dron 1994, 50, 8929. (b) Dussault, P. H.; Trullinger, T. K.; Cho-Shultz,
S. Tetrahedron 2000, 56, 9213. (c) Griesbeck, A. G.; Bartoschek, A.;
Neudorfl, J.; Miara, C. Photochem. Photobiol., 2006, 82, 1233.
(5) (a) Barnych, B.; Fenet, B.; Vatele, J.-M. Tetrahedron 2013, 69,
334.
(6) Selected examples of cyclization of hydroperoxides with vari-
ous electrophiles, see: (a) Porter, N. A.; Funk, M.; Gilmore, D.; Isaac,
R.; Nixon, J. J. Am. Chem. Soc. 1976, 98, 6000. (b) Leclercq, D.; Bats,
J.-P.; Picard, P.; Moulines, J. Synthesis, 1982, 778. (c) Xu, X.-X.; Dong,
H.-Q. J. Org. Chem. 1995, 60, 3039. (d) Li, Y.; Hao, H.-D.; Wu, Y.
Org. Lett. 2009, 11, 2691.(e) Guerra, F. M.; Zubía, E.; Ortega, M. J.;
Moreno-Dorado, F. J.; Massanet, G. M. Tetrahedron 2010, 66, 157.(f)
Dai, P.; Dussault, P. H. Org. Lett. 2005 7, 4333. (g) Holla, H.; La-
baied, M.; Pham, N.; Jenkins, I. D.; Stuart, K.; Quinn, R. J. Bioorg.
Med. Chem. Lett. 2011, 21, 4793. (h) Harris, J. R.; Waetzig, S. R.;
Woerpel, K. A. Org. Lett. 2009 11, 3290. (i) Xu, C.; Schwartz, C.;
Raible, J.; Dussault, P. H. Tetrahedron 2009, 65, 9680.
9
10
11
12
13
14
15
16
17
18
19
20
21
22
23
24
25
26
27
28
29
30
31
32
33
34
35
36
37
38
39
40
41
42
43
44
45
46
47
48
49
50
51
52
53
54
55
56
57
58
59
60
(7)(a) Fontana, A.; Gonzalez, M. C.; Gavagnin, M.; Templado, J.;
Cimino, G. Tetrahedron Lett. 2000, 41, 429. (b) Duran, R.; Zubia, E.;
Ortega, M. J.; Naranjo, S.; Salva, J. Tetrahedron 2000, 56, 6031.(c)
Fontana, A.; Cimino, G.; Gavagnin, M.; Gonzalez, M. C.; Estornell, E.
J. Med. Chem. 2001, 44, 2362. (d) Davies-Coleman, M. T.; Cantrell,
C. L.; Gustafson, K. R.; Beutler, J. A.; Pannell, L. K.; Boyd, M. R. J. Nat.
Prod. 2000, 63, 1411. (e) Reyes, F.; Rodrıguez-Acebes, R.; Fernandez,
R.; Bueno, S.; Francesch, A.; Cuevas, C. J. Nat. Prod. 2010, 73, 83.
(8)(a) Lu, X.; Liu, Y.; Sun, B.; Cindric, B.; Deng, L. J. Am. Chem.
Soc. 2008, 130, 8134. (b) For a review of asymmetric synthesis of per-
oxides, see: Sala, G. D.; Lattanzi, A. ACS Catal. 2014, 4, 1234.
(9)Dussault, P. H.; Sahli, A. J. Org. Chem. 1992, 57, 1009.
(10) (a) Frick, J. A.; Klassen, J. B.; Bathe, A.; Abramson, J. M.;
Rapoport, H. Synthesis, 1992, 621. (b) Boger, D. L.; Panek, J. S. J. Org.
Chem. 1981, 46, 1208.
(11) (a) Francais, A.; Leyva, A.; Etxebarria-Jardi, G.; Ley, S. V. Org.
Lett. 2010, 12, 340. (b) Curran, D. P.; Zhang, Q.; Richard, C.; Lu, H.;
Gudipati, V.; Wilcox, C. S. J. Am. Chem. Soc. 2006, 128, 9561.
(12) Ren, H.; Krasovskiy, A.; Knochel, P. Org. Lett. 2010, 6, 4215.
(13) Nicolaou, K. C.; Duggan, M. E.; Ladduwahetty, T. Tetrahedron
Lett. 1984, 25, 2069.
(14) Wang, Z.-X.; Tu, Y.; Frohn, M.; Zhang, J.-R.; Shi, Y. J. Am.
Chem. Soc. 1997, 119, 11224.
(15) DiLauro, A. M.; Seo, W.; Phillips, S. T. J. Org. Chem. 2011, 76,
7352.
(16) See supporting information for details.
ACS Paragon Plus Environment