R. Katsuta et al. / Tetrahedron Letters 49 (2008) 7042–7045
7045
4. Mitsunobu, O.; Yamada, M.; Mukaiyama, T. Bull. Chem. Soc. Jpn. 1967, 40, 935–
939.
11. Sidebottom, P. J.; Highcock, R. M.; Lane, S. J.; Procopiou, P. A.; Watson, N. S. J.
Antibiot. 1992, 45, 648–658.
5. Blakemore, P. R.; Cole, W. J.; Kocien´ ski, P. J.; Morley, A. Synlett 1998, 26–28.
6. Blakemore, P. R. J. Chem. Soc., Perkin Trans. 1 2002, 2563–2585.
7. Organ, M. G.; Bilokin, Y. V.; Bratovanov, S. J. Org. Chem. 2002, 67, 5176–5183.
12. Kohno, J.; Asai, Y.; Nishino, M.; Sakurai, M.; Kawano, K.; Hiramatsu, H.;
Kameda, M.; Kishi, N.; Okuda, T.; Komatsubara, S. J. Antibiot. 1999, 52, 1114–
1123.
8. Analytical and spectral data of synthesized 1: n2D51:4714.
½
a 2D5
ꢂ
+11 (c 0.35,
13. Nukina, M. T.; Marumo, S. Tetrahedron Lett. 1977, 18, 2603–2606.
14. Li, M.; Zhou, P.; Roth, H. F. Synthesis 2007, 55–60.
CH3OH). 1H NMR (500 MHz, CD3OD) d (ppm) 0.81 (3H, d, J = 6.5 Hz, 10-Me),
0.85 (3H, t, J = 7.0 Hz, 12-H), 0.89 (3H, d, J = 6.2 Hz, 8-Me), 0.97 (1H, ddd,
J = 13.0, 8.6, 4.2 Hz, 9-Ha), 1.13 (1H, m, 11-Ha), 1.2-1.35 (2H, m, 10-H, 11-Hb),
1.21 (1H, ddd, J = 13.0, 9.4, 4.7 Hz, 9-Hb), 1.5-1.6 (2H, m, 4-H), 1.95–2.15 (3H, m,
5-H, 8-H), 2.67 (3H, s, N-Me), 2.87 (1H, dd, J = 13.8, 8.3 Hz, 1-Ha), 2.96 (1H, dd,
J = 13.8, 6.0 Hz, 1-Hb), 3.22 (1H, ddd, J = 8.3, 6.0, 4.7 Hz, 2-H), 3.63 (1H, ddd,
J = 6.8, 5.3, 4.7 Hz, 3-H), 5.16 (1H, dd, J = 15.1, 8.1 Hz, 7-H), 5.27 (1H, dt, J = 15.1,
6.5 Hz, 6-H), 6.77 (2H, quasi d, J = 8.1 Hz, 30-H, 50-H), 7.11 (2H, quasi d,
J = 8.1 Hz, 20-H, 60-H). 13C NMR (125 MHz, CD3OD) d (ppm) 11.7, 19.3, 22.3,
29.3, 31.1, 31.8, 33.1, 34.1, 35.4, 35.7, 45.5, 65.9, 68.7, 116.8, 127.6, 128.3,
15. Analytical and spectral data of synthesized 2: mp 122–126 °C. ½a D25
ꢁ21 (c 0.35,
ꢂ
CH3OH). 1H NMR (500 MHz, CD3OD) d (ppm) 0.82 (3H, d, J = 6.5 Hz, 10-Me),
0.84 (3H, t, J = 7.3 Hz, 12-H), 0.91 (3H, d, J = 6.8 Hz, 8-Me), 0.99 (1H, ddd,
J = 13.5, 9.7, 4.8 Hz, 9-Ha), 1.13 (1H, m, 11-Ha), 1.22 (1H, ddd, J = 13.5, 9.7,
4.8 Hz, 9-Hb), 1.25–1.35 (2H, m, 10-H, 11-Hb), 1.45–1.6 (2H, m, 4-H), 1.99 (1H,
m, 5-Ha), 2.1–2.25 (2H, m, 5-Hb, 8-H), 2.62 (3H, s, N-Me), 2.86 (1H, dd, J = 14.7,
7.9 Hz, 1-Ha), 2.91 (1H, dd, J = 14.7, 7.0 Hz, 1-Hb), 3.34 (1H, ddd, J = 7.9, 7.0,
3.0 Hz, 2-H), 3.83 (1H, ddd, J = 9.4, 3.6, 3.0 Hz, 3-H), 5.22 (1H, dd, J = 15.5,
8.3 Hz, 7-H), 5.33 (1H, dt, J = 15.5, 6.7 Hz, 6-H), 6.78 (2H, quasi d, J = 8.5 Hz, 30-
H, 50-H), 7.10 (2H, quasi d, J = 8.5 Hz, 20-H, 60-H). 13C NMR (125 MHz, CD3OD) d
(ppm) 11.7, 19.4, 22.3, 29.9, 31.1, 32.4, 33.1, 33.2, 35.8, 45.6, 66.8, 68.7, 116.9,
131.4, 138.6, 157.9. IR (KBr)
m
= 3382, 2958, 1681, 1517, 1202 cmꢁ1. ESI-TOFMS
m/z calcd for C21H36NO2 [M+H]+ 334.2741, found 334.2773.
9. Morvai, M.; Nagy, T.; Kocsis, Á.; Szabó, L. F.; Podányi, B. Magn. Reson. Chem.
2000, 38, 343–359.
127.6, 128.4, 131.3, 138.8, 158.0. IR (KBr)
m
= 3239, 2961, 1671, 1203, 1185,
1146 cmꢁ1
334.2773.
.
ESI-TOFMS m/z calcd for C21H36NO2 [M+H]+ 334.2741, found
10. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J. Am. Chem. Soc. 1991, 113,
4092–4096.