P. Vichare, A. Chattopadhyay / Tetrahedron: Asymmetry 21 (2010) 1983–1987
1987
Am. Chem. Soc. 2003, 125, 12692; (d) Christensen, C.; Juhl, K.; Hazell, R. G.;
Jorgensen, K. A. J. Org. Chem. 2002, 67, 4875; (e) Palomo, C.; Oirbide, M.; Laso, A.
Angew. Chem., Int. Ed. 2005, 44, 3811.
was used in excess and then with 5% MeOH in CHCl3 to obtain 16 in
quantitative yield. This was immediately dissolved in MeOH
(20 mL) and mixed with solid K2CO3 (2 g). The mixture was stirred
at room temperature overnight. The solvent was removed under
reduced pressure and the residue was dissolved in CHCl3. The or-
ganic layer was washed successively with water, 5% aqueous HCl,
again water, brine, and then dried. The solvent was removed under
reduced pressure and column chromatography of the residue
(0–5% MeOH in CHCl3) afforded pure 17 as a white solid substance
5. (a) Allingham, M. T.; Howard-Jones, A.; Murphy, P. J.; Thomas, D. A.; Caulkett, P.
W. R. Tetrahedron Lett. 2003, 44, 8677; (b) Ooi, T.; Doda, K.; Maruoka, K. J. Am.
Chem. Soc. 2003, 125, 2054; (c) Li, H.; Wang, B.; Deng, L. J. Am. Chem. Soc. 2006,
128, 732; (d) Corey, E. J.; Zhang, F. Y. Angew. Chem., Int. Ed. 1999, 38, 1931; (e)
Ma, D.; Pan, Q.; Han, F. Tetrahedron Lett. 2002, 43, 9401; (f) Bernardi, L.; Fini, F.;
Herrera, R. P.; Ricci, A.; Sgarzani, V. Tetrahedron 2006, 62, 375; (g) Yoon, T. P.;
Jacobsen, E. N.; Palomo, C.; Oirbide, M.; Laso, A.; Lopez, R. J. Am. Chem. Soc.
2005, 127, 17622; (h) Yoon, T. P.; Jacobsen, E. N. Angew. Chem., Int. Ed. 2005, 44,
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6. (a) Chattopadhyay, A.; Mamdapur, V. R. J. Org. Chem. 1995, 60, 585; (b)
Chattopadhyay, A. J. Org. Chem. 1996, 61, 6104; (c) Chattopadhyay, A.; Dhotare,
B.; Hassarajani, S. A. J. Org. Chem. 1999, 64, 6874; (d) Dhotare, B.;
Chattopadhyay, A. Synthesis 2003, 1337; (e) Dhotare, B.; Chattopadhyay, A.
Tetrahedron Lett. 2005, 46, 3103; (f) Dhotare, B.; Goswami, D.; Chattopadhyay,
A. Tetrahedron Lett. 2005, 46, 6219; (g) Chattopadhyay, A.; Salaskar, A. J. Chem.
Soc., Perkin Trans. 1 2002, 785; (h) Chattopadhyay, A.; Vichare, P.; Dhotare, B.
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Tetrahedron: Asymmetry 2009, 2007, 20; (k) Vichare, P.; Chattopadhyay, A.
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Chem. 2007, 72, 9357.
(119 mg, 91.5% from 15). ½a D25
ꢁ
¼ þ16:6 (c 1.04, CHCl3); lit9m
½
a 2D4
ꢁ
¼ þ16:7 (c 1.0, CHCl3); mp 99.6–100.2 °C (lit9m mp 99.4–
100.1 °C) 1H NMR: d 0.87 (br t, 3H), 1.24 (m, 23H), 1.62 (m, 3H),
2.0 (br s 1H), 3.7–3.8 (m, 1H), 3.85 (dd, J = 3.6, 6.6 Hz, 1H), 3.97
(dd, J = 7.0, 9.0 Hz, 1H), 4.1 (m, 1H), 4.2 (dd, J = 3.4, 4.6 Hz, 1H).
13C NMR: d 14.1, 22.7, 26.0, 28.8, 29.3, 29.7, 31.9, 63.7, 68.4, 72.5,
82.1.
4.11. (2S,3S,4S)-4-Amino-2-tetradecyl-tetrahydrofuran-3-ol X
(Jaspine B)
7. Kuroda, I.; Musman, M.; Ohtani, I. I.; Ichiba, T.; Tanaka, J.; Gravalos, D. G.; Higa,
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P.; Morris, K.; Stauffer, C. S.; Datta, A. Org. Lett. 2005, 7, 875; (c) Du, Y.; Liu, J.;
Linhardt, R. J. J. Org. Chem. 2006, 71, 1351; (d) Lin, J.; Du, Y.; Dong, X.; Meng, X.;
Xiao, J.; Cheng, L. Carbohydr. Res. 2006, 341, 2653; (e) Sudhakar, N.; Kumar, A.
R.; Prabhakar, A.; Jagadeesh, B.; Rao, B. V. Tetrahedron Lett. 2005, 46, 325; (f)
Ramanna, C. V.; Giri, A. G.; Suryavanshi, S. B.; Gonnade, R. G. Tetrahedron Lett.
2007, 48, 265; (g) Reddy, L. V. R.; Reddy, P. V.; Shaw, A. K. Tetrahedron:
Asymmetry 2007, 18, 542; (h) Jayachitra, G.; Sudhakar, N.; Anchoori, P. K.; Rao,
B. V.; Roy, S.; Banerjee, R. Synthesis 2010, 115; (i) Reddipalli, G.; Venkataiah, M.;
Mishra, M. K.; Fadnavis, N. W. Tetrahedron: Asymmetry 2007, 1802, 20; (j)
Yoshimitsu, Y.; Inuki, S.; Oishi, S.; Fujii, N.; Ohno, H. J. Org. Chem. 2010, 75,
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C. P.; Litjens, R. E.; Marel, G. A. V.; Overkleeft, H. S. J. Org. Chem. 2006, 71, 836;
(p) Ribes, C.; Falomir, E.; Carda, M.; Marco, J. A. Tetrahedron 2006, 62, 5421; (q)
Abraham, E.; Candela-Lena, J. I.; Davies, S. G.; Georgiou, M.; Nicholson, R. L.;
Roberts, P. M.; Russel, A. J.; Sanchez-Fernandez, E. M.; Smith, A. D.; Thomson, J.
E. Tetrahedron: Asymmetry 2007, 18, 2510; (r) Abraham, E.; Brock, E. A.;
Candela-Lena, J. I.; Davies, S. G.; Georgiou, M.; Nicholson, R. L.; Perkin, J. H.;
Russel, A. J.; Sanchez-Fernandez, E. M.; Scott, P. M.; Smith, A. D.; Thomson, J. E.
Org. Biol. Chem. 2008, 6, 1665. and references cited therein; (s) Yakura, T.; Sato,
S.; Yoshimoto, Y. Chem. Pharm. Bull. 2007, 55, 1284; (t) Venkatesan, K.;
Srinivasan, K. V. Tetrahedron: Asymmetry 2008, 19, 209; (u) Urano, H.; Entomo,
N.; Kuwahara, S. Biosci. Biotechnol. Biochem. 2010, 74, 152; (v) Canals, D.;
Mormeneo, D.; Fabrias, G.; Llebaria, A.; Casas, J.; Delgado, A. Bioorg. Med. Chem.
2009, 17, 235; (w) Enders, D.; Teteryan, V.; Palecek, J. Synthesis 2008, 2278; (x)
Inuki, S.; Yoshimitsu, Y.; Oishi, S.; Fujii, N.; Ohno, H. Org. Lett. 2009, 11, 4478.
10. Steliou, K.; Poupart, M. J. Org. Chem. 1985, 50, 4971.
A solution of 17 (75 mg, 0.0023 mol) in a solvent mixture of
MeOH (4 mL) and CH2Cl2 (3 mL) was stirred with 10% Pd/C
(42 mg, 50 wt %) for 6 h under hydrogen atmosphere at room tem-
perature. It was then diluted with CH2Cl2 and filtered through a
pad of Celite and repeatedly washed with 5% MeOH in CH2Cl2.
The solvent was removed under reduced pressure and column
chromatography of the crude residue (0–5% MeOH in CHCl3) affor-
ded pure A as a white solid (63 mg, 91.4%) whose physical (mp
95.9–97.1 °C), specific rotation {½a D25
¼ þ17:7 (c 0.38, EtOH)} and
ꢁ
spectroscopic data were in accordance with the reported ones
{mp 96.6–97.2 °C;9m
½
a 2D4
ꢁ
¼ þ17:5 (c 0.3, EtOH)9r}.
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