1092
Y. H. Jung et al.
Letter
Synlett
Supporting Information
(11) Kim, I. S.; Li, Q. R.; Lee, J. K.; Lee, S. H.; Lim, J. K.; Zee, O. P.; Jung,
Y. H. Synlett 2007, 1711.
(12) Li, Q. R.; Kim, S. I.; Park, S. J.; Yang, H. R.; Baek, A. R.; Kim, I. S.;
Jung, Y. H. Tetrahedron 2013, 69, 10384.
Supporting information for this article is available online at
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(13) (a) Kim, I. S.; Li, Q. R.; Dong, G. R.; Kim, Y. C.; Hong, Y. J.; Lee, M.;
Chi, K.-W.; Oh, J. S.; Jung, Y. H. Eur. J. Org. Chem. 2010, 1569.
(b) Kim, I. S.; Jung, Y. H. Heterocycles 2011, 83, 2489. (c) Lee, S.
H.; Kim, I. S.; Li, Q. R.; Dong, G. R.; Jeong, L. S.; Jung, Y. H. J. Org.
Chem. 2011, 76, 10011. (d) Dong, G. R.; Hong, S.; Kim, S. I.; Kim,
I. S.; Jung, Y. H. Eur. J. Org. Chem. 2012, 4200. (e) Kim, S. J.; Jeon,
T. H.; Min, I. S.; Kim, I. S.; Jung, Y. H. Tetrahedron Lett. 2012, 53,
3680. (f) Li, Q. R.; Dong, G. R.; Park, S. J.; Hong, Y. R.; Kim, I. S.;
Jung, Y. H. Eur. J. Org. Chem. 2013, 4427. (g) Min, I. S.; Kim, S. I.;
Hong, S.; Kim, I. S.; Jung, Y. H. Tetrahedron 2013, 69, 3901.
(h) Lee, S. H.; Park, S. J.; Kim, I. S.; Jung, Y. H. Tetrahedron 2013,
69, 1877.
References and Notes
(1) (a) Ager, D. J.; Prakash, I.; Schaad, D. R. Chem. Rev. 1996, 96, 835.
(b) Cardillo, G.; Tomasini, C. Chem. Soc. Rev. 1996, 25, 117.
(c) Agrofoglio, L. A.; Challand, S. R. Acyclic, Carbocyclic and L-
Nucleosides; Kluwer Academic Publishers: Dordrecht, 1998.
(d) Crimmins, M. T. Tetrahedron 1998, 54, 9229.
(2) For a review of synthetic and biological features of the mannos-
tatins, see: Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem.
Rev. 1999, 99, 779.
(3) (a) Ando, O.; Nakajima, M.; Hamano, K.; Itoi, K.; Takahashi, S.;
Takamatsu, Y.; Sato, A.; Enokita, R.; Haruyama, H. J. Antibiot.
1993, 46, 1116. (b) Ando, O.; Satake, H.; Itoi, K.; Sato, A.;
Nakajima, M.; Takahashi, S.; Haruyama, H. J. Antibiot. 1991, 44,
1165.
(14) Dasari, B.; Jogula, S.; Borhade, R.; Balasubramanian, S.;
Chandrasekar, G.; Kitambi, S. S.; Arya, P. Org. Lett. 2013, 15, 432.
(15) Characterization Data of 6
Rf = 0.26 (CH2Cl2–MeOH–EtOH–NH4OH = 5:2:2:1); [α]25D +38.96
(c 1.0, CHCl3). 1H NMR (300 MHz, CD3OD): δ = 5.71 (d, J = 1.2 Hz,
1 H), 4.46 (d, J = 5.4 Hz, 1 H), 4.21–4.16 (m, 2 H), 3.83–3.77 (m, 2
H). 13C NMR (125 MHz, CD3OD): δ = 146.9, 128.3, 79.2, 73.3,
61.2, 59.0. HRMS (EI): m/z calcd for C6H11NO3 [M]+: 145.0739;
found: 145.0742.
(4) Yaginuma, S.; Muto, N.; Tsujino, M.; Sudate, Y.; Hayashi, M.;
Otani, M. J. Antibiot. 1981, 34, 359.
(5) Kusuka, T.; Yamamoto, H.; Shibata, M.; Muroi, M.; Kishi, T.;
Mizuno, K. J. Antibiot. 1968, 21, 255.
(6) Montgomery, J. A. Med. Res. Rev. 1982, 2, 271.
(16) Characterization Data of 7
(7) (a) Marquez, V. E.; Lim, M.-I. Med. Res. Rev. 1986, 6, 1.
(b) Saunders, J.; Cameron, J. M. Med. Res. Rev. 1995, 15, 497.
(c) Roberts, S.; Biggadike, K.; Borthwick, A. D.; Kirk, B. Topics in
Medicinal Chemistry; 1998. (d) Song, G. Y.; Paul, V.; Choo, H.;
Morrey, J.; Sidwell, R. W.; Schinazi, R. F.; Chu, C. K. J. Med. Chem.
2001, 44, 3985.
(8) (a) Kameda, Y.; Horii, S. J. Chem. Soc., Chem. Commun. 1972, 746.
(b) Asano, N.; Takeuchi, M.; Ninomiya, K.; Kameda, Y.; Matsui, K.
J. Antibiot. 1984, 37, 859. (c) Ogawa, S.; Miyamoto, Y.; Nakajima,
A. Chem. Lett. 1989, 725. (d) Ogawa, S.; Nakajima, A.; Miyamoto,
Y. J. Chem. Soc., Perkin Trans. 1 1991, 3287.
Rf = 0.17 (CH2Cl2–MeOH–EtOH–NH4OH = 5:3:3:1); [α]25 –36.8
D
(c 1.0, CHCl3). 1H NMR (300 MHz, D2O): δ = 4.43–4.39 (m, 1 H),
4.25 (d, J = 8.7 Hz, 1 H), 4.00 (d, J = 4.8 Hz, 1 H), 3.82 (d, J = 12.3
Hz, 1 H), 3.63 (d, J = 12.0 Hz, 1 H), 3.62–3.57 (m, 1 H). 13C NMR
(125 MHz, D2O): δ = 81.4, 74.1, 73.7, 67.9, 62.4, 56.7. HRMS (EI):
m/z calcd for C6H13NO5 [M]+: 179.0794; found: 179.0795.
(17) Characterization Data of 8
Rf = 0.23 (CH2Cl2–MeOH–EtOH–NH4OH = 5:2:1:1). [α]25 –42.8
D
(c 1.0, CHCl3). 1H NMR (300 MHz, D2O): δ = 4.30–4.23 (m, 2 H),
3.87 (dd, J = 7.8, 5.4 Hz, 1 H), 3.77 (s, 1 H), 3.66 (d, J = 13.2 Hz, 1
H), 3.57 (d, J = 8.1 Hz, 1 H). 13C NMR (125 MHz, D2O): δ = 74.8,
68.6, 66.2, 61.8, 57.9, 56.2. HRMS (EI): m/z calcd for C6H11NO4
[M]+: 161.0688; found: 161.0689.
(9) Mahmud, T. Nat. Prod. Rep. 2003, 20, 137.
(10) (a) Asano, N. Curr. Top. Med. Chem. 2003, 3, 471. (b) Asano, N.;
Nash, R. J.; Molyneux, R. J.; Fleet, G. W. J. Tetrahedron: Asymme-
try 2000, 11, 1645. (c) Marquez, V. E.; Lim, M. I. Med. Res. Rev.
1986, 6, 1.
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