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PAPER
Park, C. H.; Kong, X. P.; Plattner, J. J.; Leonard, J. M.;
Norbeck, D. W.; Wideburg, N. E.; Saldivar, A.; Ruiz, L.;
Kati, W. M.; Sham, H. L.; Robins, T.; Stewart, K. D.; Hsu,
A. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 2484.
1H NMR (400 MHz, CDCl3): d = 1.13 (m, 1 H), 1.35 (s, 9 H), 1.41
(s, 9 H), 1.78 (m, 1 H), 2.71 (dd, J = 6.7, 14.1 Hz, 1 H), 2.78 (dd,
J = 6.7, 14.1 Hz, 1 H), 2.89 (m, 2 H), 3.51 (m, 1 H), 3.65 (q, J = 8.2
Hz, 1 H), 4.05 (m, 1 H), 4.34 (d, J = 8.9 Hz, 1 H), 4.37 (m, 1 H),
5.03 (d, J = 8.9 Hz, 1 H), 7.12–7.30 (m, 10 H).
13C NMR (75 MHz, CDCl3): d = 28.26, 28.37, 39.09, 40.64, 41.58,
47.96, 55.79, 65.80, 78.98, 79.98, 126.04, 126.55, 128.32, 128.53,
129.16, 129.44, 137.35, 138.76, 155.96, 157.15.
(3) (a) Stoner, E. J.; Cooper, A. J.; Dickman, D. A.;
Kolaczkowski, L.; Lallaman, J. E.; Liu, J.-H.; Oliver-
Shaffer, P. A.; Patel, K. M.; Paterson, J. B.; Plata, D. J.;
Riley, D. A.; Sham, H. L.; Stengel, P. J.; Tien, J.-H. J. Org.
Process Res. Dev. 2000, 4, 264. (b) Sham, H. L.; Kempf, D.
J.; Molla, A.; Marsh, K. C.; Kumar, G. N.; Chen, C. M.; Kati,
W. M.; Stewart, K.; Lal, R.; Hsu, A.; Betebenner, D.;
Korneyeva, M.; Vasavanonda, S.; McDonald, E.; Saldivar,
A.; Wideburg, N. E.; Chen, X.; Niu, P.; Park, C.; Jayanti, V.;
Grabowski, B.; Granneman, G. R.; Sun, E.; Japour, A. J.;
Leonard, J. M.; Plattner, J.; Norbeck, D. W. Antimicrob.
Agents Chemother. 1998, 42, 3218.
(4) (a) Adamo, I.; Benedetti, F.; Berti, F.; Campaner, P. Org.
Lett. 2006, 8, 51. (b) Tossi, A.; Benedetti, F.; Norbedo, S.;
Skrbec, D.; Berti, F.; Romeo, D. Bioorg. Med. Chem. 2003,
11, 4719. (c) Benedetti, F.; Berti, F.; Norbedo, S. J. Org.
Chem. 2002, 67, 8635. (d) Ghosh, A. K.; Bilcer, G.; Schiltz,
G. Synthesis 2001, 2203. (e) Benedetti, F.; Norbedo, S.
Chem. Commun. 2001, 203. (f) Ghosh, A. K.; Shin, D.;
Mathivanan, P. Chem. Commun. 1999, 1025. (g) Haight, A.
R.; Stuk, T. L.; Allen, M. S.; Bhagavatula, L.; Fitzgerald, M.;
Hannick, S. M.; Kerdesky, F. A. J.; Menzia, J. A.; Parekh, S.
I.; Robbins, T. A.; Scarpetti, D.; Tien, J.-H. J. Org. Process
Res. Dev. 1999, 3, 94. (h) Gurjar, M. K.; Pal, S.; Rao, A. V.
R.; Pariza, R. J.; Chorgade, M. S. Tetrahedron 1997, 53,
4769. (i) Stuk, T. L.; Haight, A. R.; Scarpetti, D.; Allen, M.
S.; Menzia, J. A.; Robbins, T. A.; Parekh, S. I.; Langridge,
D. C.; Tien, J.-H. J.; Pariza, R. J.; Kerdesky, F. A. J. J. Org.
Chem. 1994, 59, 4040. (j) Kempf, D. J.; Marsh, K. C.;
Codacovi Fino, L.; Bryant, P.; Craig-Kennard, A.; Sham, H.
L.; Zhao, C.; Vasavanonda, S.; Kohlbrenner, W. E.;
Wideburg, N. E.; Saldivar, A.; Green, B. E.; Herrin, T.;
Norbeck, D. W. Bioorg. Med. Chem. 1994, 2, 847.
FABMS: m/z = 485 [M+ + 1].
Compound 5:
Mp 140–142 °C; [a]D25 –11.62 (c 1.2, CHCl3).
IR (KBr): 3370, 2992, 1686, 1669, 1524, 1172, 701 cm–1.
1H NMR (400 MHz, CDCl3): d = 1.39 (s, 18 H), 1.61 (m, 2 H), 2.72–
2.79 (m, 2 H), 2.83 (dd, J = 7.4, 13.4 Hz, 1 H), 2.88 (dd, J = 7.4,
13.4 Hz, 1 H), 3.41 (br s, 1 H), 3.59–3.71 (m, 2 H), 3.86 (m, 1 H),
4.56 (br d, 1 H), 4.81 (d, J = 8.9 Hz, 1 H), 7.08–7.30 (m, 10 H).
13C NMR (75 MHz, CDCl3): d = 28.32, 38.46, 39.73, 41.54, 50.09,
55.98, 69.90, 79.22, 79.63, 126.21, 126.42, 128.37, 129.30, 129.38,
137.56, 138.51, 155.89, 156.12.
FABMS: m/z = 485 [M+ + 1].
Acknowledgment
G.B., A.R.K. and E.R. thank the CSIR (New Delhi) for research fel-
lowships. The authors also thank Dr. J. S. Yadav, Dr. A. C. Kunwar
and Dr. T. K. Chakraborthy for their help and encouragement.
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Synthesis 2008, No. 19, 3061–3064 © Thieme Stuttgart · New York