Organic Letters
Letter
(15) Brown, S. P.; Brochu, M. P.; Sinz, C. J.; MacMillan, D. W. C. J.
Am. Chem. Soc. 2003, 125, 10808−10809.
ASSOCIATED CONTENT
* Supporting Information
The Supporting Information is available free of charge on the
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S
(16) Boonyarattanakalin, S.; Liu, X.; Michieletti, M.; Lepenies, B.;
Seeberger, P. H. J. Am. Chem. Soc. 2008, 130, 16791−16799.
(17) Omura, K.; Swern, D. Tetrahedron 1978, 34, 1651−1660.
(18) More, J. D.; Finney, N. S. Org. Lett. 2002, 4, 3001−3003.
(19) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155−4156.
(20) De Luca, L.; Giacomelli, G.; Masala, S.; Porcheddu, A. J. Org.
Chem. 2003, 68, 4999−5001.
Experimental details and related references for the
preparation of 3a−c, 6a, 6b, 7a′, 9a′, 9b′, 12, and 17;
NMR spectra and HPLC chromatograms (PDF)
(21) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277−
7287.
AUTHOR INFORMATION
Corresponding Author
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(22) (a) Hung, S. C.; Wong, C. H. Angew. Chem., Int. Ed. Engl. 1996,
35, 2671−2673. (b) Mikkelsen, L. M.; Krintel, S. L.; Jimenez-Barbero,
J.; Skrydstrup, T. J. Org. Chem. 2002, 67, 6297−6308. (c) Daragics, K.;
Notes
Fugedi, P. Tetrahedron Lett. 2009, 50, 2914−2916. (d) Ghosh, B.; Lai,
̈
Y.-H.; Shih, Y. -Y; Pradhan, T. K.; Mong, K. − K. T. Chem. - Asian J.
2013, 8, 3191−3199.
The authors declare no competing financial interest.
(23) Kumar, P.; Dwivedi, N. Acc. Chem. Res. 2013, 46, 289−299.
(24) (a) Lin, H.; Sun, X.-W.; Lin, G.-Q. Org. Lett. 2014, 16, 752−755.
(b) Nuzzi, A.; Massi, A.; Dondoni, A. Org. Lett. 2008, 10, 4485−4488.
(c) Chacko, S.; Ramapanicker, R. J. Org. Chem. 2015, 80, 4776−4782.
(25) Aspinall, G. O.; McDonald, A. G.; Sood, R. K. Can. J. Chem.
1994, 72, 247−251.
ACKNOWLEDGMENTS
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Thanks are given to the Ministry of Science and Technology of
Taiwan (MOST 102-2113-M-009-009) and the Centre of
Interdisciplinary Science of NCTU for financial support.
(26) (a) Gurjar, M. K.; Talukdar, A. Tetrahedron 2004, 60, 3267−
3271. (b) Garegg, P. J.; Oscarson, S.; Szonye, M. Carbohydr. Res. 1990,
̈
REFERENCES
■
205, 125−132. (c) Khare, N. K.; Sood, R. K.; Aspinall, G. O. Can. J.
(1) Granstrom, T. B.; Takata, G.; Tokuda, M.; Izumori, K. J. Biosci.
Bioeng. 2004, 97, 89−94.
(2) Holst, O. In Structure of the Lipopolysaccharide Core Region in
Bacterial Lipopolysaccharide; Knirel, Y. A. Valvano, M. A., Eds.;
Springer-Verlag: Wien, 2011.
(3) Kosma, P. Curr. Org. Chem. 2008, 12, 1021−1039.
(4) Majumder, M.; Mukherjee, A. K. Carbohydr. Res. 1983, 122, 209−
216.
(5) (a) Ashmus, R. A.; Lowary, T. L. Org. Lett. 2014, 16, 2518−2521.
(b) St. Michael, F.; Szymanski, C.-M.; Li, J.-J.; Chan, K.-H.; Khieu, N.-
H.; Larocque, S.; Wakarchuk, W.-W.; Brisson, J.-R.; Monteiro, M.-A.
Eur. J. Biochem. 2002, 269, 5119−5136.
Chem. 1994, 72, 237−246.
(27) Hayashi, Y.; Yamaguchi, J.; Sumiya, T.; Hibino, K.; Shoji, M. J.
Org. Chem. 2004, 69, 5966−5973.
(28) Cordova, A.; Sunden, H.; Bogevig, A.; Johansson, M.; Himo, F.
Chem. - Eur. J. 2004, 10, 3673−3684.
(29) Only trace of undesired diastereomer was identified in HPLC. In
reporting the dr, an estimated value of >95:5 was given, which
according to literature corresponds to the detection limit of
uncalibrated HPLC analysis: Wernerova, M.; Hudlicky, T. Synlett
2010, 2010, 2701−2707.
(30) CH3CN was also examined at 0 °C, but the yield (60%) was
lower than that given by the use of DMF/DMSO mixture.
(6) Nakazawa, F. Carbohydr. Res. 1985, 143, 185−190.
(7) (a) Dziewiszek, K.; Banaszek, A.; Zamojski, A. Tetrahedron Lett.
1987, 28, 1569−1572. (b) Boons, G. J. P. H.; van der Klein, P. A. M.;
van der Marel, G. A.; van Boom, J. H. Recl. Trav. Chim. Pays-Bas. 1988,
107, 507−508. (c) Bernlind, C.; Bennett, S.; Oscarson, S. Tetrahedron:
Asymmetry 2000, 11, 481−492. (d) Yamasaki, R.; Takajyo, A.; Kubo,
H.; Matsui, T.; Ishii, K.; Yoshida, M. J. Carbohydr. Chem. 2001, 20,
171−180. (e) Segerstedt, E.; Mannerstedt, K.; Johansson, M.; Bernlind,
C.; Oscarson, S. J. Carbohydr. Chem. 2004, 23, 443−452. (f) Kim, M.;
Grzeszczyk, B.; Zamojski, A. Tetrahedron 2000, 56, 9319−9337.
(g) Durka, M.; Buffet, K.; Li, T.; Tikad, A.; Hagen, B.; Vincent, S. P.
Carbohydr. Chem.: Proven Synthetic Methods 2014, 2, 77−83. (h) van
Straten, N. C. R.; Kriek, N. M. A. J.; Timmers, C. M.; Wigchert, S. C.
M.; van der Marel, G. A.; van Boom, J. H. J. Carbohydr. Chem. 1997, 16,
947−966.
́ ́
(31) Dohi, H.; Perion, R.; Durka, M.; Bosco, M.; Roue, Y.; Moreau, F.;
Grizot, S.; Ducruix, A.; Escaich, S.; Vincent, S. P. Chem. - Eur. J. 2008,
14, 9530−9539.
(32) Dasser, M.; Chret
1 1990, 3091−3094.
́
ien, F.; Chapleur, Y. J. Chem. Soc., Perkin Trans.
(33) Kano, A.; Fukumoto, T.; Ohtani, K.; Yoshihara, A.; Ohara, T.;
Tajima, S.; Izumori, K.; Tanaka, K.; Ohkouchi, T.; Ishida, Y.; Nishizawa,
Y.; Ichimura, K.; Tada, Y.; Gomi, K.; Akimitsu, K. J. Exp. Bot. 2013, 64,
4939−4951.
(34) Capila, I.; Linhardt, R. J. Angew. Chem., Int. Ed. 2002, 41, 390−
412.
(35) (a) Hansen, S. U.; Dalton, C. E.; Barath, M.; Kwan, G.; Raftery,
́
J.; Jayson, G. C.; Miller, G. J.; Gardiner, J. M. J. Org. Chem. 2015, 80,
3777−3789. (b) Hansen, S. U.; Barath, M.; Salameh, B. A. B.; Pritchard,
R. G.; Stimpson, W. T.; Gardiner, J. M.; Jayson, G. C. Org. Lett. 2009,
11, 4528−4531 and references cited therein.
(8) (a) Brimacombe, J. S.; Kabir, A. K. M. S. Carbohydr. Res. 1986,
152, 329−334. (b) Jorgensen, M.; Iversen, E. H.; Madsen, R. J. Org.
Chem. 2001, 66, 4625−4629. (c) Crich, D.; Banerjee, A. Org. Lett.
2005, 7, 1395−1398. (d) Guzlek, H.; Graziani, A.; Kosma, P.
Carbohydr. Res. 2005, 340, 2808−2811. (e) Crich, D.; Banerjee, A. J.
Am. Chem. Soc. 2006, 128, 8078−8086. (f) Dohi, H.; Perion, R.; Durka,
M.; Bosco, M.; Roue, Y.; Moreau, F.; Grizot, S.; Ducruix, A.; Escaich, S.;
Vincent, S. P. Chem. - Eur. J. 2008, 14, 9530−9539.
(36) Zulueta, M. M. L.; Zhong, Y.-Q.; Hung, S.-C. Chem. Commun.
2013, 49, 3275−3287.
(37) Chao, C. S.; Lin, C. Y.; Mulani, S. K.; Hung, W. C.; Mong, K. K.
T. Chem. - Eur. J. 2011, 17, 12193−12202.
(38) Reported hexofuranosyl diastereomers: Stepowska, H.;
Zamojski, A. Tetrahedron 1999, 55, 5519−5538.
̌
(39) Moravcova,
61−66.
́
J.; Capkova,
́
J.; Stanek
̌
, J. Carbohydr. Res. 1994, 263,
(9) Ohara, T.; Adibekian, A.; Esposito, D.; Stallforth, P.; Seeberger, P.
H. Chem. Commun. 2010, 46, 4106−4108.
(10) Stanetty, C.; Baxendale, I. R. Eur. J. Org. Chem. 2015, 2015,
2718−2726.
(11) In ESI of: Sasaki, E.; Lin, C.-I.; Lin, K.-Y.; Liu, H.-W. J. Am. Chem.
Soc. 2012, 134, 17432−17435.
(12) Stepowska, H.; Zamojski, A. Tetrahedron 1999, 55, 5519−5538.
(13) Xu, G.; Moeller, K. D. Org. Lett. 2010, 12, 2590−2593.
(14) Zhong, G. Angew. Chem., Int. Ed. 2003, 42, 4247−4250.
5539
Org. Lett. 2015, 17, 5536−5539