Paper
RSC Advances
7 (a) D. Crich and A. Banerjee, J. Am. Chem. Soc., 2007, 129,
10064–100065; (b) C. Haase, H. Rohde and O. Seitz, Angew.
Chem., Int. Ed., 2008, 47, 6807–6810; (c) J. Chen, Q. Wan,
Y. Yuan, J. Zhu and S. J. Danishefsky, Angew. Chem., Int.
Ed., 2008, 47, 8521–8524.
8 (a) R. Yang, K. K. Pasunooti, F. Li, X.-W. Liu and C.-F. Liu, J.
Am. Chem. Soc., 2009, 131, 13592–13593; (b) J. Chen, P. Wang,
J. Zhu, Q. Wan and S. J. Danishefsky, Tetrahedron, 2010, 66,
2277–2283; (c) J. Chen, P. Wang, J. Zhu, Q. Wan and
S. J. Danishefsky, Tetrahedron, 2010, 66, 2277–2283; (d)
Z. Tan, S. Shang and S. J. Danishefsky, Angew. Chem., Int.
Ed., 2010, 49, 9500–9503; (e) S. Shang, Z. Tan, S. Dong and
S. J. Danishefsky, J. Am. Chem. Soc., 2011, 133, 10784–
10786; (f) P. Siman, S. V. Karthikeyan and A. Brik, Org.
Lett., 2012, 14, 1520–1523; (g) L. R. Malins, K. M. Cergol
and R. J. Payne, ChemBioChem, 2013, 14, 559–563; (h)
D. D. Dhavale, Tetrahedron Lett., 2010, 51, 6745–6747 and
references cited therein. For a review on 5-hydroxy-lysine
see: (j) K. R. Herbert, G. M. Williams, G. J. S. Cooper and
M. A. Brimble, Org. Biomol. Chem., 2012, 10, 1137–1144;
For Lys: (k) P. F. Hughes, S. H. Smith and J. T. Olson, J.
Org. Chem., 1994, 59, 5799–5802; For Glu: (l) T. Kunieda,
T. Ishizuka, T. Higuchi and M. Hirobe, J. Org. Chem., 1988,
53, 3381–3383; (m) H. Takahata, Y. Banba, M. Tajima and
T. Momose, J. Org. Chem., 1991, 56, 240–245; (n)
H. Takahata, Y. Banba, M. Tajima and T. Momose, J. Org.
Chem., 1991, 56, 240–245; (o) S. Shiokawa, T. Ohta and
S. Nozoe, Chem. Pharm. Bull., 1992, 40, 1398–1399; (p)
N. D-Uomo, M. C. D-Giovannia, D. Misiti, G. Zappia and
G. D. Monache, Liebigs Ann. Chem., 1994, 641–644; (q)
L. Tamborini, P. Conti, A. Pinto, S. Colleoni, M. Gobbi and
C. D. Micheli, Tetrahedron, 2009, 65, 6083–6089.
R. E. Thompson, B. Chan, L. Radom, K. A. Jolliffe and 11 For multiple target oriented hydroxy amino acid synthesis
R. J. Payne, Angew. Chem., Int. Ed., 2013, 52, 9723–9727; (i)
K. M. Cergol, R. E. Thompson, L. R. Malins, P. Turner and
R. J. Payne, Org. Lett., 2014, 16, 290–293; (j)
S. D. Townsend, Z. Tan, S. Dong, S. Shang, J. A. Brailsford
and S. J. Danishefsky, J. Am. Chem. Soc., 2012, 134, 3912–
3916.
see: (a) Y. N. Belokon, A. G. Bulychev, S. V. Vitt,
Y. T. Struchkov, A. S. Batsanov, T. V. Timofeeva,
V. A. Tsyryapkin, M. G. Ryzhov, L. A. Lysova,
V. I. Bakhrnutov and V. M. Belikov, J. Am. Chem. Soc., 1985,
107, 4252–4259; (b) S. S. Norio, B. M. Inabaf, T. Moriwaket
and S. Torii, Tetrahedron Lett., 1985, 26, 5309–5312; (c)
D. A. Evans, E. B. Sjogren, A. E. Weberm and R. E. Conn,
Tetrahedron Lett., 1987, 28, 39–42; (d) D. A. Evans and
A. E. Weber, J. Am. Chem. Soc., 1987, 109, 7151–7157; (e)
9 (a) D. D. Van Slyke and A. Hiller, Proc. Natl. Acad. Sci. U. S. A.,
1921, 7, 185–186; (b) J. C. Sheeham, K. Maeda, A. K. Sen and
J. A. Stock, J. Am. Chem. Soc., 1962, 84, 1303–1305; (c)
W. Traub and K. A. Piez, Adv. Protein Chem., 1971, 25, 243–
352; (d) H. Maehr, C.-M. Liu, N. J. Palleroni, J. Smallheer,
L. Todan, T. H. Williams and J. F. Blount, J. Antibiot., 1986,
39, 17–25; (e) T. A. Smitka, J. B. Deeter, A. H. Hunt,
F. P. Mertz, R. M. Ellis, L. D. Boeck and R. C. Yao, J.
Antibiot., 1988, 41, 726–733; (f) A. A. Tymiak,
T. J. McCormick and S. E. Unger, J. Org. Chem., 1989, 54,
1149–1157; (g) S. Omura, T. Fujimoto, K. Otoguro,
R. Koriguchi, H. Tanaka and Y. Sasaki, J. Antibiot., 1991,
44, 113–116; (h) S. Omuro, K. Matsuzaki, T. Fujimoto,
K. Kosuge, T. Furuya, S. Fujita and A. Nakagawa, J.
Antibiot., 1991, 44, 117–118; (i) S. Chatterjee,
D. K. Chatterjee, R. H. Jani, J. Blumbach, B. N. Ganguli,
N. Klesel, M. Limbert and G. Siebert, J. Antibiot., 1992, 45,
839–845; (j) For amino acids as enzyme inhibitors see:
C. Walsh, Tetrahedron, 1982, 38, 871–909; (k) A. I. Ayi and
R. Guedj, J. Chem. Soc., Perkin Trans. 1, 1983, 2045–2051.
10 For mono target oriented hydroxy amino acid synthesis see:
ˆ
M. Hirama, H. Hioki and S. Ito, Tetrahedron Lett., 1988, 29,
3125–3128; (f) R. C. Roemmele and H. Rapoport, J. Org.
Chem., 1989, 54, 1866–1875; (g) M. A. Blaskovich and
G. A. Lajoie, J. Am. Chem. Soc., 1993, 115, 5021–5030; (h)
M. A. Blaskovich and G. A. Lajoie, J. Am. Chem. Soc., 1993,
115, 5021–5030; (i) Y. N. Belokon, K. A. Kochetkov,
N. S. Ikonnikov, T. V. Strelkova, S. R. Harutyunyan and
A. S. Saghiyan, Tetrahedron: Asymmetry, 2001, 12, 481–485;
(j) B. Ma, J. L. Parkinson and S. L. Castle, Tetrahedron Lett.,
2007, 48, 2083–2086; (k) S. G. Davies, A. M. Fletcher,
A. B. Frost, J. A. Lee, P. M. Roberts and J. E. Thomson,
Tetrahedron, 2013, 69, 8885–8898; (l) S. C. Deshmukh and
P. Talukdar, J. Org. Chem., 2014, 79, 11215–11225; (m)
Y. Singjunla, J. Baudoux and J. Rouden, Org. Lett., 2013,
15, 5770–5773; (n) K. Makino, T. Goto, Y. Hiroki and
Y. Hamada, Angew. Chem., Int. Ed., 2004, 43, 882–882.
12 (a) D. R. Spring, Org. Biomol. Chem., 2003, 1, 3867–3870; (b)
D. S. Tan, Nat. Chem. Biol., 2005, 1, 74–84.
For-leu: (a) D. Seebach, E. Juaristi, D. D. Miller, C. Schickli 13 (a) K. S. A. Kumar, M. Haj-Yahya, D. Olschewski,
and T. Weber, Helv. Chim. Acta, 1987, 70, 237–261; (b)
D. A. Evans, E. B. Sjogren, A. E. Weber and R. E. Conn,
Tetrahedron Lett., 1987, 28, 39–42; (c) M. E. Jung and
Y. H. Jung, Tetrahedron Lett., 1989, 48, 6637–6640; (d)
C. G. Cald Well and S. S. Bondy, Synthesis, 1990, 34–35; (e)
E. J. Corey, D. H. Lee and S. Choi, Tetrahedron Lett., 1992,
33, 6735–6738; (f) J. S. Yadav, S. Chandrasekhar,
R. Y. Reddy and A. V. R. Rao, Tetrahedron, 1995, 51, 2749–
2754; For Pro: (g) S. Hanessian and S. P. Sahoo, Can. J.
H. A. Lashuel and A. Brik, Angew. Chem., Int. Ed., 2009, 48,
8090–8094; (b) Z. Harpaz, P. Siman, K. S. A. Kumar and
A. Brik, ChemBioChem, 2010, 11, 1232–1235; (c)
K. S. A. Kumar, Bioorg. Med. Chem., 2013, 21, 3609–3613;
(d) V. P. Vyavahare, C. Chakraborty, B. Maity,
S. Chattopadhyay, V. G. Puranik and D. D. Dhavale, J. Med.
Chem., 2007, 50, 5519–5523; (e) K. S. A. Kumar,
J. S. Rathee, M. Subramanian and S. Chattopadhyay, J. Org.
Chem., 2013, 78, 7406–7413.
Chem., 1984, 62, 1400–1402; (h) J. Cooper, P. T. Gallagher 14 N. Nepomniaschiy, V. Grimminger, A. Cohen, S. DiGiovanni,
and D. W. Knight, J. Chem. Soc., Chem. Commun., 1988,
509–510; (i) N. B. Kalamkar, V. M. Kasture and
H. Lashuel and A. Brik, Org. Lett., 2008, 11, 5243–5524 and
references cited therein.
This journal is © The Royal Society of Chemistry 2015
RSC Adv., 2015, 5, 19455–19464 | 19463