Helvetica Chimica Acta – Vol. 96 (2013)
1569
(300 MHz, CDCl3): 7.28 – 7.37 (m, 5 arom. H); 7.08 (d, J ¼ 8.3, 2 arom. H); 6.88 (d, J ¼ 8.3, 2 arom. H);
5.02 (s, PhCH2); 4.83 (br. s, CꢀOH); 3.55 – 3.77 (m, CꢀCH, CHN); 3.51 (br. s, CHꢀOH); 2.90 (dt, J ¼ 6.0,
14.3, 1 H, CH2); 2.75 – 2.81 (m, MeN, 1 H of CH2); 1.32 (s, MeC). 13C-NMR (75 MHz, CDCl3): 175.1;
157.8; 136.8; 130.0; 128.7; 128.5; 127.9; 127.4; 115.3; 74.6; 73.3; 70.1; 67.4; 36.7; 28.9; 23.94. HR-ESI-MS:
364.1522 ([M þ Na]þ, C20H21NNaOþ4 ; calc. 364.1523).
(3S,4S,5S)-3,4-Dihydroxy-5-[(4-hydroxyphenyl)methyl]-1,3-dimethylpyrrolidin-2-one (1). To a soln.
of 9 (0.052 g, 0.152 mmol) in MeOH (1.0 ml) was added Pd/C (0.005 g, 10 mol-%), and the mixture was
stirred under H2 for 6 h. After completion of the reaction, the mixture was filtered through a Celite pad
and concentrated under reduced pressure. The residue was purified by CC (AcOEt/hexane 8 :2) to give 1
(0.027 g, 72%). White solid. M.p. 177 – 1788. [a]2D5 ¼ þ17.8 (c ¼ 0.15, MeOH). IR (KBr): 3380, 2898, 1678,
1615, 1524, 1430, 1380, 1240, 1076. 1H-NMR (500 MHz, (D6)acetone): 7.12 (d, J ¼ 8.2, 2 arom. H); 6.80 (d,
J ¼ 8.2, 2 arom. H); 3.68 – 3.63 (m, CHO); 3.54 (ddd, J ¼ 3.2, 5.4, 7.3, CHN); 2.99 (dd, J ¼ 14.6, 5.4, 1 H,
CH2); 2.79 (dd, J ¼ 7.3, 15.5, 1 H, CH2); 2.78 (s, MeN); 1.24 (s, MeC). 13C-NMR (75 MHz, (D6)acetone):
175.2; 157.3; 131.8 (2 C); 129.7; 116.8 (2 C); 76.1; 74.2; 67.6; 37.4; 29.2; 24.3. HR-ESI-MS: 274.1068
([M þ Na]þ, C13H17NNaOþ4 ; calc. 274.1055).
REFERENCES
[1] S. Isaacs, R. Berman, Y. Kashman, T. Gebreyesus, T. Yosief, J. Nat. Prod. 1991, 54, 83; S. Aoki, K.
Higuchi, Y. Ye, R. Satari, M. Kobayashi, Tetrahedron 2000, 56, 1833; M. Daferner, T. Anke, O.
Sterner, Tetrahedron 2002, 58, 7781; N. U. Sata, S. Wada, S. Matsunaga, S. Watabe, R. W. M. Soest, N.
Fusetani, J. Org. Chem. 1999, 64, 2331; K. JoMon, Y. Kuroda, M. Ajisaka, H. Sakai, J. Antibiot. 1972,
25, 271; S. Sakuda, M. Ono, K. Furihata, J. Nakayama, A. Suzuki, A. Isogai, J. Am. Chem. Soc. 1996,
118, 7855.
[2] Y. Wang, C. Long, F. Yang, X. Wang, Q. Sun, H. Wang, Y. Shi, G. Tang, J. Nat. Prod. 2009, 72, 1151;
A. P. Michael, E. J. Grace, M. Kotiw, R. A. Barrow, J. Nat. Prod. 2002, 65, 1360; J. Y. Li, G. Strobel, J.
Harper, E. Lobkovsky, J. Clardy, Org. Lett. 2000, 2, 767; G. Lang, A. L. J. Cole, J. W. Blunt, M. H. G.
Munro, J. Nat. Prod. 2006, 69, 151; J. Ondeyka, G. Harris, D. L. Zink, A. Basilio, F. Vicente, G. Bills,
G. Platas, J. Collado, A. Gonzalez, M. Cruz, J. Martin, J. N. Kahn, S. Galuska, N. Giacobbe, G.
Abruzzo, E. Hickey, P. Liberator, B. Jiang, D. Xu, T. Roemer, S. B. Singh, J. Nat. Prod. 2009, 72, 134.
[3] A. I. Laskin, H. A. Lechevalier, ꢂCRC Handbook of Microbiologyꢃ, 2nd edn., 5, CRC Press, Inc.;
Boca Raton, FL, 1984, and refs. cit. therein.
[4] J. Li, S.-C. Liu, S.-B. Niu, W.-Y. Zhuang, Y.-S. Che, J. Nat. Prod. 2009, 72, 2184.
[5] P. Radha Krishna, M. Alivelu, T. P. Rao, Eur. J. Org. Chem. 2012, 3, 616.
[6] P. Radha Krishna, K. Lopinti, Synlett 2007, 1742; P. Radha Krishna, A. Srishailam, Tetrahedron Lett.
2007, 48, 6924; P. Radha Krishna, G. Dayaker, Tetrahedron Lett. 2007, 48, 7279; P. Radha Krishna,
B. K. Reddy, Tetrahedron Lett. 2010, 51, 6262; P. Radha Krishna, B. K. Reddy, P. Srinivas,
Tetrahedron 2012, 68, 841.
[7] P. Radha Krishna, P. S. Reddy, J. Comb. Chem. 2008, 10, 426.
[8] P. Radha Krishna, K. Anitha, Tetrahedron Lett. 2011, 52, 4546.
[9] G.-Y. Chen, H. Huang, J.-L. Ye, A.-E. Wang, H.-Y. Huang, H.-K. Zhang, P.-Q. Huang, Chem. – Asian
J. 2012, 7, 504.
[10] A. K. Chatterjee, R. H. Grubbs, Angew. Chem., Int. Ed. 2002, 41, 3171; R. H. Grubbs, Tetrahedron
2004, 60, 7117.
[11] a) S. Papst, A. F. M. Noisier, M. A. Brimble, Y. Yang, G. W. Krissansen, Bioorg. Med. Chem. 2012,
20, 5139; b) X.-C. Cheng, R.-L. Wang, Z.-K. Dong, J. Li, Y.-Y. Li, R.-R. Li, Bioorg. Med. Chem. 2012,
20, 5738; c) S. Hanazawa, M. A. Arai, X. Li, M. Ishibashi, Bioorg. Med. Chem. Lett. 2008, 18, 95;
d) W. L. Scott, J. G. Martynow, J. C. Huffman, M. J. OꢃDonnel, J. Am. Chem. Soc. 2007, 129, 7077;
e) C. Sorg, E. Rꢁde, O. Westphal, Justus Liebigs Ann. Chem. 1970, 734, 180; f) M. J. Oila, J. E. Tois,
A. M. P. Koskinen, Tetrahedron 2005, 61, 10748; g) C. Wolf, C. J. Francis, P. A. Hawes, M. Shah,
Tetrahedron: Asymmetry 2002, 13, 1733; h) H. Sajiki, K. Hirota, Tetrahedron 1998, 54, 13981; i) L. S.
Richter, T. R. Gadek, Tetrahedron Lett. 1994, 35, 4705.