S. Hajra et al. / Tetrahedron Letters 49 (2008) 3625–3627
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2. (a) Lertvorachon, J.; Meepowpan, P.; Thebtaranonth, Y. Tetrahedron
1998, 54, 14341; (b) Mandal, P. K.; Maiti, G.; Roy, S. C. J. Org.
Chem. 1998, 63, 2829; (c) Ghatak, A.; Sarkar, S.; Ghosh, S.
Tetrahedron 1997, 53, 17335; (d) Damon, R. E.; Schlessinger, R. H.
Tetrahedron Lett. 1976, 41, 4065; (e) Martin, J.; Watts, P. C.;
Johnson, F. J. Org. Chem. 1974, 39, 1676; (f) van Tamelen, E. E.;
Bach, S. R. J. Am. Chem. Soc. 1958, 80, 3079.
6. Hajra, S.; Giri, A. K.; Karmakar, A.; Khatua, S. Chem. Commun.
2007, 2408.
7. (a) Heathcock, C. H.; Arseniyadis, S. Tetrahedron Lett. 1985, 26,
6009; (b) Van Draanen, N. A.; Arseniyadis, S.; Crimmins, M. T.;
Heathcock, C. H. J. Org. Chem. 1991, 56, 2499.
8. (2S,3R)-5-oxo-2-pentyl-tetrahydrofuran-3-carboxylic acid [(ꢀ)-13]: A
29
white solid; mp 103–105 °C, (lit.3k mp 105–107 °C); ½aꢁD ꢀ54.19 (c
21
3. Asymmetric synthesis of 4,5-trans-paraconic acids: (a) Hon, Y.-S.;
Hsieh, C.-H.; Liu, Y.-W. Tetrahedron 2005, 61, 2713; (b) Ariza, X.;
Fernandez, N.; Garcia, J.; Lopez, M.; Montserrat, L.; Ortiz, J.
Synthesis 2004, 128; (c) Barros, M. T.; Maycock, C. D.; Ventura, M.
R. Org. Lett. 2003, 5, 4097; (d) Chhor, R. B.; Nosse, B.; Sorgel, S.;
Bohm, C.; Seitz, M.; Reiser, O. Chem. Eur. J. 2003, 9, 260 ; (e) Sibi,
M. P.; Liu, P.; Ji, J.; Hajra, S.; Chen, J. J. Org. Chem. 2002, 67, 1738;
(f) Bo¨hm, C.; Reiser, O. Org. Lett. 2001, 3, 1315; (g) Kongsaeree, P.;
Meepowpan, P.; Thebtaranonth, Y. Tetrahedron: Asymmetry 2001,
12, 1913; (h) Bella, M.; Margarita, R.; Orlando, C.; Orsini, M.;
Parlanti, L.; Piancatelli, G. Tetrahedron Lett. 2000, 41, 561; (i)
Chandrasekharam, M.; Liu, R.-S. J. Org. Chem. 1998, 63, 9122; (j)
Sibi, M. P.; Ji, J. Angew. Chem., Int. Ed. 1997, 36, 274; (k) Sibi, M. P.;
Deshpande, P. K.; Loggia, A. J. L. Synlett 1996, 343; (l) Martin, T.;
Rodriguez, C. M.; Martin, V. S. J. Org. Chem. 1996, 61, 6450; (m)
Takahata, H.; Uchida, Y.; Momose, T. J. Org. Chem. 1995, 60, 5628;
(n) Mawson, S. D.; Weavers, R. T. Tetrahedron 1995, 51, 11257; (o)
Zhu, G.; Lu, X. J. Org. Chem. 1995, 60, 1087; (p) Zhu, G.; Lu, X.
Tetrahedron: Asymmetry 1995, 6, 885; (q) Vaupel, A.; Knochel, P.
Tetrahedron Lett. 1995, 36, 231; (r) Mulzer, J.; Salimi, N.; Hart, H.
Tetrahedron: Asymmetry 1993, 4, 457; (s) Azevedo, M. B. M.; Murta,
M. M.; Greene, A. E. J. Org. Chem. 1992, 57, 4567.
4. Asymmetric synthesis of 4,5-cis-paraconic acids: (a) Amador, M.;
Ariza, X.; Garcia, J.; Ortiz, J. J. Org. Chem. 2004, 69, 8172; (b)
Forster, A. B.; Fitremann, J.; Renaud, P. Helv. Chim. Acta 2002, 85,
3965; (c) Drioli, S.; Felluga, F.; Forzato, C.; Nitti, P.; Pitacco, G.;
Valentin, E. J. Org. Chem. 1998, 63, 2385; (d) Jacobi, P. A.;
Herradura, P. Tetrahedron Lett. 1996, 37, 8297; (e) Zhang, Z.; Lu, X.
Tetrahedron: Asymmetry 1996, 7, 1923; (f) Mulzer, J.; Kattner, L.;
Strecker, A. R.; Schroeder, C.; Buschmann, J.; Lehmann, C.; Luger,
P. J. Am. Chem. Soc. 1991, 113, 4218.
0.52, CHCl3), [lit.3s ½aꢁD ꢀ54.0 (c 0.50, CHCl3)]; 1H NMR (200 MHz,
CDCl3): d 4.61 (q, J = 5.3 Hz, 1H), 3.20–3.00 (m, 1H), 3.00–2.65 (m,
2H), 1.90–1.65 (m, 2H), 1.60–1.15 (m, 6H), 1.00–0.75 (m, 3H). 13C
NMR (50 MHz, CDCl3): d 175.3, 173.6, 82.2, 48.6, 34.8, 31.7, 30.9,
24.5, 22.0, 13.5. Anal. Calcd for C10H16O4: C, 59.98; H, 8.05. Found:
C, 59.81; H, 8.23.
(2R,3S)-5-oxo-2-pentyl-tetrahydrofuran-3-carboxylic acid [(+)-13]: A
29
white solid; mp 104–105 °C, ½aꢁD +54.08 (c 0.51, CHCl3);
spectroscopic data (1H NMR, 13C NMR) are identical with
(ꢀ)- 13; Anal. Calcd for C10H16O4: C, 59.98; H, 8.05. Found: C,
60.53; H, 8.27.
9. (2S,3S)-5-oxo-2-(1E-pentenyl) tetrahydrofuran-3-carboxylic acid
29
[(ꢀ)-14]: A gummy liquid, ½aꢁD ꢀ31.28 (c 0.51, CHCl3); 1H NMR
(400 MHz, CDCl3): d 5.89 (dt, J = 15.2, 6.6 Hz, 1H), 5.45 (dd,
J = 15.2, 7.6 Hz, 1H), 5.14 (t, J = 7.6 Hz, 1H), 3.56 (q, J = 7.6 Hz,
1H), 2.97 (dd, J = 17.6, 7.2 Hz, 1H), 2.68 (dd, J = 17.6, 8.7, 1H), 2.06
(q, J = 6.7 Hz, 2H), 1.55–1.15 (m, 2H), 0.88 (t, J = 8.0 Hz, 3H). 13C
NMR (50 MHz, CDCl3): d 175.8, 172.7, 137.6, 122.8, 80.6, 44.9, 33.9,
31.0, 21.6, 13.2. Anal. Calcd for (C10H16O4 + 0.25H2O): C, 59.25; H,
7.21. Found: C, 59.28; H, 7.64.
(2S, 3S)-5-oxo-2-(1E-pentenyl)-tetrahydrofuran-3-carboxylic acid
29
[(+)-14]: ½aꢁD +31.28 (c 0.51, CHCl3). Spectroscopic data (1H NMR,
13C NMR) are identical with (ꢀ)-14.
10. (2S,3S,4S)-4-Methyl-5-oxo-2-pentyl-tetrahydrofuran-3-carboxylic
acid [(ꢀ)-Phaseolinic acid][(ꢀ)-5]: A white solid; mp = 138–140 °C
29
(lit.1b,4a mp = 136–137 °C), ½aꢁD ꢀ113.95 (c 0.50, CHCl3), [lit.1b,4a
[a]D ꢀ114.4 (c 1.46, CHCl3)]; 1H NMR (200 MHz, CDCl3): d 4.65 (dt,
J = 8.3, 5.4 Hz, 1H), 3.24 (dd, J = 9.7, 8.4 Hz, 1H), 3.15–2.95 (m,
1H), 1.60–1.50 (m, 2H), 1.50–1.30 (m, 2H), 1.30–1.20 (m, 4H), 1.31 (d,
J = 7.0 Hz, 3H), 0.88 (t, J = 7.0 Hz, 3H). 13C NMR (50 MHz,
CDCl3): d 177.3, 175.0, 77.6, 51.4, 36.3, 31.4, 31.1, 25.3, 22.6, 14.5,
13.8. Anal. Calcd for (C11H18O4 + 0.33H 2O): C, 59.98; H, 8.54.
Found: C, 59.75; H, 8.30.
5. Asymmetric synthesis of both 4,5-trans- and cis-paraconic acids: (a)
Blanc, D.; Madec, J.; Popowyck, F.; Ayad, T.; Phansavath, P.;
Ratovelomanana-Vidal, V.; Genet, J.-P. Adv. Synth. Catal. 2007, 349,
943; (b) Ariza, X.; Garcia, J.; Lopez, M.; Montserrat, L. Synlett 2001,
120; (c) Masaki, Y.; Arasaki, H.; Itoh, A. Tetrahedron Lett. 1999, 40,
4829.
(2R,3R,4R)-4-Methyl-5-oxo-2-pentyl-tetrahydrofuran-3-carboxylic
acid [(+)-5]: (+)-phaseolinic acid. (1H NMR, 13C NMR) are identical
29
with (ꢀ)-phaseolinic acid (ꢀ)-5. ½aꢁD +114.04 (c 0.50, CHCl3).