6636
G. Mehta, H. M. Shinde / Tetrahedron Letters 46 (2005) 6633–6636
127.27, 67.83, 41.36, 27.01 (3C), 25.82 (3C), 20.91, 19.56,
References and notes
18.04, ꢀ3.83, ꢀ4.54; HRMS calcd for C36H52Si2O4 (M+
23
Na): 627.3302 found: 627.3315; (+)-22 ½aꢁD +150.0
1. Chu, M.; Mierzwa, R.; Xu, L.; He, L.; Terracciano, J.;
Patel, M.; Gullo, V.; Black, T.; Zhao, W.; Chan, T.;
Mcphail, A. T. J. Nat. Prod. 2003, 66, 1527.
(c 0.22, CHCl3); IR (neat) 3449, 2930, 2855, 1726 cmꢀ1
;
1H NMR (300 MHz, CDCl3): d 7.66 (t, J = 7.5 Hz, 4H),
7.45–7.34 (m, 6H), 5.62 (d, J = 9.6 Hz, 1H), 5.40 (dd,
J = 9.6 and 4.8 Hz, 1H), 5.05–4.95 (m, 1H), 4.07 (t,
J = 3.6 Hz, 1H), 3.91–3.86 (m, 1H), 2.63–2.56 (m, 1H),
2.12–2.05 (m, 3H), 1.97–1.79 (m, 2H), 1.67–1.45 (m, 7H),
1.27 (d, J = 6.6 Hz, 3H), 1.04 (s, 9 H); 13C NMR
(75 MHz, CDCl3): 175.44, 136.19, 135.89, 134.39, 133.72,
133.38, 129.89, 129.60, 129.38, 127.78, 127.31, 72.08,
71.20, 69.59, 41.86, 39.24, 31.57, 27.08 (3C), 24.79,
22.87, 19.56; HRMS calcd for C30H40SiO4 (M+Na):
´
2. (a) Bouche, J.-P.; Zechel, K.; Kornberg, A. J. Biol. Chem.
1975, 250, 5995; (b) Arai, K.-I.; Kornberg, A. Proc. Natl.
Acad. Sci. U.S.A. 1979, 76, 4308; (c) Richet, H.; Moham-
med, J.; McDonald, L. C.; Jarvis, W. R. Emerg. Infect.
Dis. 2001, 7, 319; (d) Grompe, M.; Versalovic, J.; Koeuth,
T.; Lupski, J. R. J. Bacterial. 1991, 173, 1268; (e)
Shrimankar, P.; Stordal, L.; Maurer, R. J. J. Bacterial.
1992, 174, 7689.
3. Jayasuriya, H.; Zink, D. L.; Polishook, J. D.; Bills, G. F.;
Dombrowski, A. W.; Genilloud, O.; Pelacz, F. F.;
Herranz, L.; Quamina, D.; Lingham, R. B.; Danzeizem,
R.; Graham, P. L.; Tomassini, J. E.; Singh, S. B. Chem.
Biodiversity 2005, 2, 112.
4. Mehta, G.; Shinde, H. M. Chem. Commun. 2005, 3703.
5. (a) Takano, S.; Higashi, Y.; Kamikubo, T.; Moriya, M.;
Ogaswara, K. Synthesis 1993, 948; (b) Konno, H.;
Ogaswara, K. Synthesis 1999, 1135; (c) Mehta, G.; Islam,
K. Synlett 2000, 1473.
24
515.2594 found: 515.2599; (+)-2 ½aꢁD +110.0 (c 0.4,
CH3OH); IR (neat) 3437, 2924, 2853, 1724, 1681 cmꢀ1
;
1H NMR (300 MHz, CDCl3): 6.97 (dd, J = 9.9 and
6.0 Hz, 1H), 5.94 (d, J = 9.9 Hz, 1H), 5.00–4.92 (m, 1H),
4.22 (dd, J = 6.0 and 3.3 Hz, 1H), 2.81 (dt, J = 12.3 and
3.9 Hz, 1H), 2.59–2.37 (m, 3H), 2.10–1.99 (m, 1H), 1.96–
1.77 (m, 2H), 1.72–1.41 (m, 4H), 1.28 (d, J = 6.0 Hz, 3H),
1.05 (m, 1H); 13C NMR (75 MHz, CDCl3): 202.54, 176.42,
148.49, 130.26, 74.41, 68.79, 47.78, 42.30, 40.03, 32.04,
25.76, 22.73, 22.25, 21.40; HRMS calcd for C14H20O4
(M+Na): 275.1259 found: 275.1265.
6. All new compounds were fully characterized on the basis
of IR, 1H NMR, 13C NMR and mass data. Spectral
26
7. Podraza, K. F.; Bassfield, R. L. J. Org. Chem. 1989, 54,
5919.
data of selected compounds: (+)-8 ½aꢁD ꢀ31.4 (c 1.4,
CHCl3); IR (neat) 2935, 2860, 1709 cmꢀ1 1H NMR
;
8. Gemal, A. L.; Luche, J. L. J. Am. Chem. Soc. 1981, 103,
5454.
(300 MHz, CDCl3): d 6.16 (dd, J = 5.4 and 3.3 Hz, 1H),
6.02 (dd, J = 5.4 and 3.3 Hz, 1H), 5.80–5.67 (m, 1H),
5.00–4.92 (m, 2H), 3.90 (m, 1H), 3.31 (br s, 1H), 3.12 (br s,
1H), 2.87–2.77 (m, 2H), 2.36–1.72 (m, 6H), 1.38–1.34 (m,
1H), 1.27–1.24 (m, 2H), 0.95 (s, 9H), 0.14 (s, 3H), 0.08 (s,
3H); 13C NMR (75 MHz, CDCl3): 212.61, 138.29, 136.98,
135.35, 114.59, 73.47, 51.98, 49.46, 47.20, 45.92, 44.80,
43.58, 36.55, 31.39, 30.50, 25.95 (3C), 18.12, ꢀ3.92, ꢀ4.87;
HRMS calcd for C21H34SiO2 (M+Na): 369.2226
9. Crystal data: X-ray data were collected at 293 K on a
SMART CCD–BRUKER diffractometer with graph-
˚
ite monochromated MoKa radiation (k = 0.7107 A). The
structure was solved by direct methods (SIR92). Refine-
ment was by full-matrix least-squares procedures on F2
using SHELXL-97. The non-hydrogen atoms were refined
anisotropically whereas the hydrogen atoms were placed
in geometrically idealised positions and constrained to ride
on their parent atoms. Compound (ꢀ)-14: C19H19NO6,
MW = 357, colourless crystal, crystal system: orthorhom-
bic, space group P212121: cell parameters: a = 4.8563(7)
25
found: 369.2213; (ꢀ)-9 ½aꢁD ꢀ109.7 (c 0.72, CHCl3); IR
1
(neat) 2930, 2858, 1735, 1686 cmꢀ1; H NMR (300 MHz,
CDCl3): d 6.78 (dd, J = 10.2 and 2.1 Hz, 1H), 5.95 (dd,
J = 10.2 and 2.1 Hz, 1H), 5.85–5.70 (m, 1H), 5.06–4.96
(m, 2H), 4.41–4.37 (m, 1H), 4.19–4.11 (m, 2H), 2.78–2.54
(m, 3H), 2.24–2.03 (m, 3H), 1.79–1.76 (m, 1H), 1.65–1.45
(m, 1H), 1.27 (t, J = 7.2 Hz, 3H), 0.92 (s, 9H), 0.15 (s,
3H), 0.13 (s, 3H); 13C NMR (75 MHz, CDCl3): 199.36,
172.24, 152.36, 137.77, 127.57, 115.02, 69.92, 60.60, 46.26,
45.83, 32.17, 27.47, 25.70 (3C), 17.93, 14.15, 9.18, ꢀ4.14,
ꢀ4.80; HRMS calcd for C20H34SiO4 (M+Na): 389.2124
˚
˚
˚
˚
A,
b = 15.617(2) A,
A , Z = 4, Dc = 1.32 g cmꢀ3
mmꢀ1
c = 23.622(4) A,
V = 1791.50
3
,
F(000) = 752, l = 0.10
.
Total number of ls parameters = 235, R1 =
0.0835 for 2558 Fo > 4sig(Fo) and 0.1066 for all 3159
data. wR2 = 0.1888, GOF = 1.155, Restrained GOF =
1.155 for all data. Crystallographic data (without structure
factors) have been deposited with the Cambridge Crystallo-
graphic Data Centre (CCDC 275655).
26
found: 389.2135; (ꢀ)-11 ½aꢁD ꢀ27.5 (c 1.2, CHCl3);
IR (neat) 3450, 2929, 2858, 1731.8 cmꢀ1 1H NMR
;
10. Seebach, D.; Hungerbuhler, E.; Naef, R.; Schnurrenber-
¨
ger, P.; Weidmann, B.; Zuger, M. Synthesis 1982, 138.
¨
(300 MHz, CDCl3): d 5.87–5.69 (m, 3H), 5.06–4.94 (m,
2H), 4.19–4.10 (m, 3H), 3.93 (d, J = 6.3 Hz, 1H), 2.67–
2.48 (m, 2H), 2.23–2.03 (m, 4H), 1.79–1.56 (m, 2H), 1.49–
1.37 (m, 1H), 1.26 (t, J = 7.2 Hz, 3H), 0.89 (s, 9H), 0.08 (s,
3H), 0.07 (s, 3H); 13C NMR (75 MHz, CDCl3): 174.30,
138.30, 132.83, 128.46, 114.68, 69.33, 65.28, 60.51, 41.22,
37.33, 33.90, 30.08, 28.07, 25.76 (3C), 17.94, 14.19, ꢀ4.17,
ꢀ4.79; HRMS calcd for C20H36SiO4 (M+Na): 391.2281
11. For recent reviews on RCM, see: (a) Grubbs, R. H.;
Chang, S. Tetrahedron 1998, 54, 4413; (b) Blechert, S.;
Schuster, M. Angew. Chem., Int. Ed. 1997, 36, 2036; (c)
Furstner, A. Angew. Chem., Int. Ed. 2000, 39, 3012; (d)
¨
Trnka, T. M.; Grubbs, R. H. Acc. Chem. Res. 2001, 34, 18;
(e) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-
VCH: Weinheim, Germany, 2003; Vol. 2.
23
12. (a) Ghosh, A. K.; Cappiello, J.; Shin, D. Tetrahedron
found: 391.2281; (+)-20 ½aꢁD +87.5 (c 0.4, CHCl3);
IR (neat) 2929, 2856, 1724 cmꢀ1 1H NMR (300 MHz,
;
Lett. 1998, 39, 4651; (b) Furstner, A.; Langemann, K.
¨
J. Am. Chem. Soc. 1997, 119, 9130; (c) Koskinen,
A. M. P.; Nevalainen, M. Angew. Chem., Int. Ed. 2001, 40,
4060.
CDCl3): d 7.72–7.66 (m, 4H), 7.47–7.34 (m, 6H), 5.74 (br s,
2H), 5.56 (d, J = 9.9 Hz, 1H), 5.40 (dd, J = 10.2 and
3.0 Hz, 1H), 5.34–5.30 (m, 1H), 4.10 (s, 1H), 3.85 (br s,
1H), 2.59–2.51 (m, 1H), 2.40–1.58 (m, 7H), 1.39 (d,
J = 6.3 Hz, 3H), 1.04 (s, 9 H), 0.94 (s, 9H), 0.08 (s, 6H);
13C NMR (75 MHz, CDCl3): 175.22, 136.14, 135.91,
134.38, 134.20, 133.36, 129.94, 129.85, 129.46, 127.76,
13. Scholl, M.; Ding, S.; Lee, C. W.; Grubbs, R. H. Org. Lett.
1999, 1, 953.
14. Blair, I. A.; Saleh, S.; Prakash, C. Tetrahedron Lett. 1989,
30, 19.