P. Janardhan Reddy et al. / Tetrahedron Letters 53 (2012) 4051–4053
4053
6. Furrow, M. E.; Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 68, 6776.
7. Bonini, C.; Chiummiento, L.; Lopardo, M. T.; Pullex, M.; Colobert, F.; Solladie, G.
Tetrahedron Lett. 2003, 44, 2695.
8. Barry, C. St. J.; Crosby, S. R.; Harding, J. R.; Hughes, R. A.; King, C. D.; Parker, G.
D.; Willis, C. L. Org. Lett. 2003, 5, 2429.
9. (a) Yadav, J. S.; Chander, M. C.; Joshi, B. V. Tetrahedron Lett. 1988, 29, 2737; (b)
Yadav, J. S.; Chander, M. C.; Rao, C. S. Tetrahedron Lett. 1989, 30, 5455; (c) Yadav,
J. S.; Deshpande, P.; Sharma, G. V. M. Tetrahedron 1990, 46, 7033.
10. (a) Birch, A. J. J. Chem. Soc. 1944, 430; (b) Birch, A. J.; Subba Rao, G. S. R. Adv. Org.
Chem. 1972, 8, 1.
11. (a) Birch, A. J.; Mani, N. S.; Subba Rao, G. S. R. J. Chem. Soc., Perkin Trans. 1 1990,
1423; (b) Kanakum, C. C.; Mani, N. S.; Ramanathan, H.; Subba Rao, G. S. R. J.
Chem. Soc., Perkin Trans. 1 1907, 1989.
butyldimethylsilyloxy) heptyl)-4,6-dimethoxybenzoate (6): Rf 0.50 (20% EtOAc
in hexane); ½a 3D1
ꢁ
= +28.6 (c 1.5, CHCl3); 1H NMR (CDCl3, 300 MHz): d 6.33 (1H, d,
J = 2.2 Hz), 6.27 (1H, d, J = 2.2 Hz), 3.83 (3H, s), 3.79 (3H, s), 3.78 (3H, s), 3.72–
3.64 (1H, m), 2.76 (1H, dd, J = 5.2, 13.5 Hz), 2.57 (1H, dd, J = 7.5, 12.8 Hz), 1.56
(1H, t, J = 6.7 Hz), 1.50–1.28 (6H, m), 0.89–0.81 (21H, m), 0.03–0.01 (9H, m),
ꢀ0.03 (3H, m); 13C NMR (CDCl3, 75 MHz): d 160.9, 139.2, 107.6, 70.6, 69.8, 56.0,
55.3, 52.0, 46.1, 42.0, 39.7, 25.8, 18.5, 14.2, ꢀ4.2, ꢀ4.6; IR (KBr): tmax 3440,
2955, 2857, 1727, 1604, 1464 cmꢀ1; ESI-MS: m/z 577 [M+Na]; HRMS (ESI)
calcd for C29H54NaO6Si2: 577.3356, found: 577.3305. 7-Desmethoxyfusarentin
methyl ether (2): Rf 0.70 (80% EtOAc in hexane); ½a D31
ꢁ
= ꢀ43.6 (c 1.0, CHCl3); 1
H
NMR (acetone-d6, 300 MHz): d 6.53 (1H, d, J = 2.2 Hz), 6.47 (1H, d, J = 2.2 Hz),
4.58 (1H, m), 3.88 (3H, s), 3.86–3.82 (4H, m), 2.91–2.85 (2H, m), 1.82 (1H, ddd,
J = 2.4, 9.2, 14.0 Hz), 1.61 (1H, ddd, J = 3.2, 10.0, 13.4 Hz), 1.49–1.38 (4H, m),
0.91 (3H, t, J = 7.1 Hz); 13C NMR (acetone-d6, 75 MHz): d 166.1, 164.8, 162.9,
146.2, 108.8, 105.9, 99.4, 75.9, 67.8, 57.1, 56.9, 44.5, 42.1, 37.0, 20.4, 15.4; IR
12. (a) Dean, F. M.; Goodchild, J.; Houghton, L. E.; Martin, J. A.; Morton, R. B.;
Parton, B.; Price, A. W.; Somvichien, N. Tetrahedron Lett. 1966, 35, 4153; (b)
Jenner, G.; Papadopoulos, M. High Pressure Research: An International Journal
1988, 1, 67.
(KBr): t
max 3465, 2956, 1707, 1604, 1462 cmꢀ1; ESI-MS: m/z 295 [M+H]; HRMS
(ESI)
calcd
for
C
16H22O5Na:
317.1359,
found:
317.1348.
ꢁ = ꢀ16.0 (c 2.0,
7-
13. Spectral
butyldimethylsilyloxy)dec-2-ynoate (7): Rf 0.30 (10% EtOAc in hexane);
= +10.6 (c 0.75, CHCl3); 1H NMR (CDCl3, 500 MHz): d 3.96–3.92 (1H, m),
data
for
selected
compounds:
(5S,7S)-Methyl-5,7-bis(tert-
Desmethoxyfusarentin (1): Rf 0.60 (40% EtOAc in hexane); ½a D31
CHCl3); 1H NMR (CDCl3, 500 MHz): d 11.15 (1H, s), 6.33 (1H, d, J = 2.0 Hz), 6.22
(1H, d, J = 2.0 Hz), 4.86–4.79 (1H, m), 4.07–4.01 (1H, m), 3.82 (3H, s), 2.94–2.82
(2H, m), 1.98–1.90 (2H, m), 1.71–1.64 (1H, m), 1.53–1.34 (4H, m), 0.95 (3H, t,
J = 7.0 Hz); 13C NMR (CDCl3, 75 MHz): d 169.7, 165.8, 164.5, 141.0, 106.2, 101.6,
99.4, 76.2, 67.0, 55.5, 42.2, 40.1, 33.7, 18.7, 14.0; IR(KBr): vmax 3443, 1661,
½ ꢁ
a 2D0
3.79–3.75 (1H, m), 3.74 (3H, s), 2.53–2.41 (1H, m), 1.73–1.62 (1H, m), 1.49–
1.29 (6H, m), 0.94–0.83 (21H, m), 0.11 (3H, s), 0.09 (3H, s), 0.07 (3H, s), 0.06
(3H, s); 13C NMR (CDCl3, 75 MHz): d 81.5, 70.1, 69.4, 68.9, 45.0, 40.3, 28.2, 25.9,
25.8, 18.3, 14.2, ꢀ3.8, ꢀ4.1, ꢀ4.6; IR (KBr):
1466 cmꢀ1; ESIMS: m/z 465 [M+Na]; HRMS (ESI) calcd for C23H46NaO4Si2
465.28214, found: 465.28268. Methyl 2-((2S,4S)-2,4-bis(tert-
v
max 3424, 2955, 2858, 2240, 1720,
1628, 1512, 1420 cmꢀ1
15H20O5Na: 303.1200, found: 303.1202.
; ESI-MS: m/z 303 [M+Na]; HRMS (ESI) calcd for
C