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D. K. Mohapatra et al.
LETTER
Mikami, Y.; Kobayashi, J. J. Nat. Prod. 2003, 66, 412.
77.6, 69.9, 64.6, 55.2, 43.5, 23.3; MS (ESI): m/z = 237 [M +
H]+, 259 [M + Na]+; HRMS (ESI): m/z [M + H]+ calcd for
C14H20O3Na: 259.1310; found: 259.1318.
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2006, 45, 6086. (b) Deiters, A.; Martin, S. F. Chem. Rev.
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(e) Love, J. A. In Handbook of Metathesis; Grubbs, R. H.,
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Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18. (g) Fürstner,
A. Angew. Chem. Int. Ed. 2000, 39, 3012. (h) Maier, M. E.
Angew. Chem. Int. Ed. 2000, 39, 2073. (i) Grubbs, R. H.;
Chang, S. Tetrahedron 1998, 54, 4413. (j) Armstrong, S. K.
J. Chem. Soc., Perkin Trans. 1 1998, 371. (k) Gerlach, K.;
Quitschalle, M.; Kalesse, M. Tetrahedron Lett. 1999, 40,
3553. (l) Nevalainen, M.; Koskinen, A. M. P. Angew. Chem.
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(12) Ravelo, J. L.; Rodriguez, C. M.; Martin, V. S. J. Organomet.
Chem. 2006, 691, 5326; and references therein.
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8019.
(14) (a) Balkrishna, S. B.; Childers, W. E. Jr.; Pinnick, H. W.
Tetrahedron 1981, 37, 2091. (b) Dalcanale, E.; Montanari,
F. J. Org. Chem. 1986, 51, 567.
(15) Analytical and spectral data of 18: [a]D27 –30.5 (c 2.7,
CHCl3); IR (KBr): 3426, 2929, 2865, 1709, 1610, 1513,
1455, 1250 cm–1; 1H NMR (300 MHz, CDCl3): d = 7.16 (d,
J = 8.7 Hz, 2 H), 6.8 (d, J = 8.7 Hz, 2 H), 5.77–5.65 (m, 1 H),
5.25–5.2 (m, 2 H), 4.51 (d, J = 11.4 Hz, 1 H), 4.25 (d,
J = 11.4 Hz, 1 H), 3.77 (s, 3 H), 3.77–3.70 (m, 1 H), 2.41 (t,
J = 7.3 Hz, 2 H), 1.91–1.78 (m, 2 H); 13C NMR (75 MHz,
CDCl3): d = 179.4, 159.0, 138.0, 130.2, 129.3, 117.6, 113.6,
78.7, 69.7, 55.1, 30.0, 29.9; MS (ESI): m/z = 273 [M + Na]+;
HRMS (ESI): m/z [M + H]+ calcd for C14H18O4Na:
273.1102; found: 273.1101.
(5) Perepogu, A. K.; Raman, D.; Murty, U. S. N.; Rao, V. J.
Bioorg. Chem. 2009, 37, 46.
(6) (a) Mohapatra, D. K.; Sahoo, G.; Ramesh, D. K.; Sastry,
G. N. Chem. Eur. J. 2009, submitted. (b) Ghosh, S.; Rao,
R. V. Tetrahedron Lett. 2007, 48, 6937. (c) Mohapatra,
D. K.; Ramesh, D. K.; Giardello, M. A.; Chorghade, M. S.;
Gurjar, M. K.; Grubbs, R. H. Tetrahedron Lett. 2007, 48,
2621. (d) Fürstnet, A.; Nagano, T.; Müller, C.; Seidel, G.;
Müller, O. Chem. Eur. J. 2007, 13, 1452. (e) Prasad, K. R.;
Penchalaiah, K.; Choudhary, A.; Anbarsan, P. Tetrahedron
Lett. 2007, 48, 309. (f) Sharma, G. V. M.; Cherukupalli,
G. R. Tetrahedron: Asymmetry 2006, 17, 1081. (g) Garćia-
Fortanet, J.; Murga, J.; Falomir, E.; Carda, M.; Marco, J. A.
J. Org. Chem. 2005, 70, 9822. (h) Matsuda, M.; Yamazaki,
T.; Fuhshuku, K.; Sugai, T. Tetrahedron 2007, 63, 8752.
(i) Gurjar, M. K.; Karmakar, S.; Mohapatra, D. K.
Tetrahedron Lett. 2004, 45, 4525. (j) Salaskar, A.; Sharma,
A.; Chattopadhyay, S. Tetrahedron: Asymmetry 2006, 17,
325. (k) Boruwa, J.; Gogoi, N.; Barua, N. C. Org. Biomol.
Chem. 2006, 4, 3521. (l) Nanda, S. Tetrahedron Lett. 2005,
46, 3661. (m) Arai, M.; Morita, N.; Aoyagi, S.; Kibayashi,
C. Tetrahedron Lett. 2000, 41, 1199.
(16) Analytical and spectral data of 15: [a]D27 –55.3 (c 1.9,
CHCl3); IR (KBr): 2923, 2853, 1729,1613, 1513, 1377, 1248
cm–1; 1H NMR (300 MHz, CDCl3): d = 7.28–7.24 (m, 4 H),
6.91–6.85 (m, 4 H), 5.80–5.68 (m, 2 H), 5.29–5.13 (m, 5 H),
4.54 (d, J = 11.5 Hz, 1 H), 4.51 (d, J = 11.3 Hz, 1 H), 4.27
(d, J = 11.3 Hz, 1 H), 4.21 (d, J = 11.5 Hz, 1 H), 3.82 (s, 3
H), 3.80 (s, 3 H), 3.80–3.72 (m, 2 H), 2.41–2.18 (m, 2 H),
1.96–1.67 (m, 4 H), 1.21 (d, J = 6.2 Hz, 3 H); 13C NMR (75
MHz, CDCl3): d = 172.8, 159.0, 138.5, 138.3, 130.5, 130.3,
129.6, 129.3, 117.5, 117.0, 113.7, 79.1, 76.3, 69.9, 69.8,
67.6, 55.2, 42.2, 30.5, 30.4, 20.5; MS (ESI): m/z = 491 [M +
Na]+; HRMS (ESI): m/z [M + H]+ calcd for C28H36O6Na:
491.2409; found: 491.2413.
(17) Analytical and spectral data of 3: [a]D27 +46.2 (c 1.0,
CHCl3); IR (KBr): 3443, 2923, 2855, 1717, 1647, 1448,
1368, 1243 cm–1; 1H NMR (300 MHz, CDCl3): d = 5.58 (dd,
J = 15.6, 9.2 Hz, 1 H), 5.41 (dd, J = 15.6, 9.0 Hz, 1 H), 5.14
(dq, J = 11.1, 6.4 Hz, 1 H), 4.15–4.05 (m, 2 H), 2.32–2.25
(m, 1 H), 2.04 (m, 3 H), 1.92–1.71 (m, 2 H), 1.22 (d, J = 6.4
Hz, 3 H); 13C NMR (75 MHz, CDCl3): d = 174.6, 135.8,
132.8, 74.3, 71.8, 67.8, 43.2, 34.3, 31.5, 21.3; MS (ESI):
m/z = 223 [M + Na]+.
(7) (a) Guindon, Y.; Yoakim, C.; Bernstein, M. A.; Morton,
H. E. Tetrahedron Lett. 1985, 26, 1185. (b) Takemura, T.;
Nishi, Y.; Takahashi, S.; Kobayashi, J.; Nakata, T.
Tetrahedron 2002, 58, 6359; and references therein.
(8) Gao, Y.; hanson, R. M.; Klunder, J. M.; Ko, S. Y.;
Masamune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987,
109, 5765.
(18) Analytical and spectral data of 33: [a]D27 +14.7 (c 1.4,
EtOH); IR (KBr): 2931, 2859, 1731, 1645, 1461, 1370, 1248
cm–1; 1H NMR (300 MHz, CDCl3): d = 5.45 (dd, J = 15.8,
9.0 Hz, 1 H), 5.30 (dd, J = 15.8, 8.6 Hz, 1 H), 5.14–5.03 (m,
1 H), 4.08–3.97 (m, 2 H), 2.26–2.20 (m, 1 H), 2.05–1.96 (m,
2 H), 1.95–1.84 (m, 1 H), 1.78–1.71 (m, 2 H), 1.18 (d,
J = 6.6 Hz, 3 H), 0.86 (s, 9 H), 0.85 (s, 9 H), 0.04 (s, 6 H),
0.02 (s, 6 H); 13C NMR (75 MHz, CDCl3): d = 174.4, 135.1,
132.4, 75.3, 73.0, 67.5, 44.8, 35.5, 31.5, 25.7, 21.4, 18.1,
–4.3, –4.4, –4.7; MS (ESI): m/z = 429 [M + H]+; HRMS
(ESI): m/z [M + H]+ calcd for C22H44O4NaSi2: 451.2675;
found: 451.2675.
(9) Reddy, L. V. R.; Sagar, R.; Shaw, A. K. Tetrahedron Lett.
2006, 47, 1753.
(10) Rama Rao, A. V.; Murthy, V. S.; Sharma, G. V. M.
Tetrahedron Lett. 1995, 36, 139.
(11) Analytical and spectral data of 17: [a]D27 –30.4 (c 1.8,
CHCl3); IR (KBr): 3456, 2922, 2853, 1616, 1513, 1247
cm–1; 1H NMR (300 MHz, CDCl3): d = 7.16 (d, J = 9.0 Hz,
2 H), 6.73 (d, J = 9.0 Hz, 2 H), 5.80–5.68 (m, 1 H), 5.23–
5.14 (m, 2 H), 4.51–4.48 (m, 1 H), 4.48 (d, J = 11.3 Hz, 1 H),
4.19 (d, J = 11.3 Hz, 1 H), 4.01–3.94 (m, 1 H), 3.73 (s, 3 H),
1.67–1.50 (m, 2 H), 1.07 (d, J = 6.8 Hz, 3 H); 13C NMR (75
MHz, CDCl3): d = 159.2, 138.1, 129.4, 128.6, 117.1, 113.8,
Synlett 2009, No. 13, 2129–2132 © Thieme Stuttgart · New York