[1] Potts, B. C. M.; Faulkner, D. J.; Chan, J. A.; Simolike, G. C.; Offen, P.; Hemling, M. E.; Francis, T. A. J. Am. Chem. Soc. 1991, 113, 6321. [2] Fan, X. D.; Flentke, G. R.; Rich, D. H. J. Am. Chem. Soc. 1998, 120, 8893. [3] Pika, J.; Faulkner, D. J. Nat. Prod. Lett. 1995, 7, 291. [4] Salomon, C. E.; Williams, D. H.; Lobkovsky, E.; Clardy, J. C.; Faulkner, D. J. Org. Lett. 2002, 4, 1699. [5] (a) Jia, Y.-X.; Wu, B.; Li, X.; Ren, S.-K.; Tu, Y.-Q.; Chan, A. S. C.; Kitching, W. Org Lett. 2001, 3, 847.(b) Jia, Y.-X.; Li, X.; Wu, B.; Zhao, X.-Z.; Tu, Y.-Q. Tetrahedron 2002, 58, 1697. [6] Shapiro, R. H.; Heath, M. J. J. Am. Chem. Soc. 1967, 89, 5734. [7] Danben, W. G.; Michno, D. M. J. Org. Chem. 1977, 42, 682. [8] Suga, T.; Imamura, K. Bull. Chem. Soc. Jpn. 1972, 45, 2060. [9] Henbest, H. B.; Wilson, R. A. L. J. Chem. Soc. 1959, 1958. [10] (a) Gignere, R. J.; Hoffimann, M. R. Tetrahedron Lett. 1981, 22, 5039. (b) Reggl, L.; Friedman, S.; Wender, I. J. Org. Chem. 1958, 23, 1136. [11] Martin, S. F.; Dodge, J. A. Tetrahedron Lett. 1991, 32, 3017. [12] Ward, D. E.; Rhee, C. K. Synth. Commun. 1988, 18, 1927. [13] (3R,4S,6R)-3,4-di[(tert-butyl dimethylsilyl)oxy]-7-hydroxy-6-methylheptan-2-one (5) [α]D25-10.0 (c 1.5, CHCl3); 1H NMR (CDCl3, 200 MHz) δ: 4.09 (d, J=3.6 Hz, 1H, 3-H), 3.94~3.92 (m, 1H, 4-H), 3.42 (dd, J=5.1, 5.8 Hz, 2H, OCH2), 2.20 (s, 3H, 1-H), 1.73~0.80 (m, 4H, OH, 5-H, and 6-H), 0.94 [s, 9H, C(CH3)3], 0.92 (d, J=4.0 Hz, 3H, CH3), 0.90 [s, 9H, C(CH3)3], 0.09 (s, 3H, SiCH3), 0.07 (s, 3H, SiCH3), 0.06 (s, 3H, SiCH3), 0.04 (s, 3H, SiCH3); 13C NMR (CDCl3, 100 MHz) δ: 210.7, 80.6, 73.6, 68.1, 37.9, 32.0, 28.3, 25.8 (6C), 18.2, 18.0, 17.4, -4.4, -4.7, -4.8, -5.1; FAB-MS m/z (%): 405 (M++1, 5), 387 (80), 347 (24), 245 (14), 215 (100), 115 (100); HRMS (ESI) calcd for C20H44Si2O4Na (M+Na)+ 427.2670, found 427.2673. |