R. J. Cox, R. M. Williams / Tetrahedron Letters 43 (2002) 2149–2152
2151
Scheme 4.
References
11. All new compounds were fully characterized by 1H and
13C NMR, IR and low and high resolution mass spec-
troscopy; (a) 2-(1,1-dimethylallyl)-6-methoxy-1H-indole
(11). Pale yellow oil which darkens on standing. 1H
NMR (300 MHz) (CDCl3) l CHCl3: 1.49 (6H, s), 3.85
(3H, s), 5.13 (2H, m), 6.05 (1H, dd, J=10.4 Hz, J=17.3
Hz), 6.25 (1H, dd, J=0.8 Hz, J=2.3 Hz), 6.77 (1H, dd,
J=2.3 Hz, J=8.9 Hz), 6.84 (1H, d, J=2.1 Hz), 7.44 (1H,
d, J=8.4 Hz), 7.80 (1H, br s). 13C NMR (74.47 MHz)
(CDCl3) l CDCl3: 27.7 (q), 38.5 (s), 56.0 (q), 94.7 (d),
97.8 (d), 109.4 (d), 112.2 (t), 120.8 (d), 122.9 (s), 136.7 (s),
144.7 (s), 146.4 (d), 156.0 (s). IR (NaCl, neat): 3418, 2967,
2834, 1627, 1459, 1246, 1159, 809 cm−1. MS (FAB+): 215
(M+, 100%), 201 (19.5). HRMS (FAB), calcd for
C14H17NO (M+): 215.1317. Found: 215.1310; (b) 2-(1,1-
dimethylallyl)-4-methoxy-1H-indole (12). Pale yellow oil
which darkens on standing. 1H NMR (300 MHz)
(CDCl3) l CHCl3: 1.49 (6H, s), 3.97 (3H, s), 5.12 (2H,
m), 6.04 (1H, dd, J=10.4 Hz, J=17.4 Hz), 6.44 (1H, dd,
J=0.6 Hz, J=2.1 Hz), 6.52 (1H, d, J=7.8 Hz), 6.95 (1H,
d, J=8.1 Hz), 7.07 (1H, t, J=7.8 Hz), 7.90 (1H, br s).
13C NMR (74.47 MHz) (CDCl3) l CDCl3: 27.8 (q), 38.5
(s), 55.6 (q), 95.3 (d), 99.8 (d), 104.3 (d), 112.4 (t), 119.1
(s), 122.3 (d), 137.4 (s), 144.5 (s), 146.3 (d), 153.0 (s). IR
(NaCl, neat): 3417, 2967, 2836, 1591, 1508, 1361, 1249,
1118, 766 cm−1. MS (FAB+): 215 (M+, 100%), 200 (6.1).
HRMS (FAB), calcd for C14H17NO (M+): 215.1317.
Found: 215.1312; (c) 2-(1,1-dimethylallyl)-1H-indol-6-ol
(13). Cream-colored crystals. Mp 130–131°C (recryst.
1. (a) Ondeyka, J. G.; Goegelman, R. T.; Schaeffer, J. M.;
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J. M.; Blizzard, T. A.; Ondeyka, J.; Goegelman, R.;
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4. See for example (a) Williams, R. M.; Cao, J.; Tsujishima,
H. Angew. Chem., Int. Ed. 2000, 39, 2540–2544; (b)
Stocking, E. M.; Sanz-Cervera, J. F.; Unkefer, C. J.;
Williams, R. M. Tetrahedron 2001, 57, 5303–5320 and
references cited therein.
5. Sanz-Cervera, J. F.; Williams, R. M. J. Am. Chem. Soc.
2002, 124, 0000.
6. (a) Martin, T.; Moody, C. J. J. Chem. Soc., Perkin Trans.
1 1988, 241–246; (b) Yogo, M.; Ito, C.; Furukawa, H.
Chem. Pharm. Bull. 1991, 39, 328–334; (c) Kno¨lker, H. J.;
Hofmann, C. Tetrahedron Lett. 1996, 37, 7947–7950.
7. (a) Houghton, E.; Saxton, J. E. J. Chem. Soc. (C) 1969,
595–599; (b) Houghton, E.; Saxton, J. E. J. Chem. Soc.
(C) 1969, 1003–1012; (c) Plieninger, H.; Sirowej, H.
Chem. Ber. 1971, 104, 1869–1870; (d) Plieninger, H.;
Sirowej, H. Chem. Ber. 1971, 104, 2027–2029; (e) Russell,
R. A. Aust. J. Chem. 1975, 28, 2535–2538; (f) Tomita, K.;
Terada, A.; Tachikawa, R. Heterocycles 1976, 4, 733–737;
(g) Tachikawa, R.; Terada, A.; Tomita, K.; Iwaoka, T.
Heterocycles 1977, 8, 695–717; (h) Das, B. C.; Fourrey,
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1
ether/hexanes). H NMR (300 MHz) (CDCl3) l CHCl3:
1.48 (6H, s), 5.13 (2H, m), 5.33 (1H, br s), 6.04 (1H, dd,
J=10.4 Hz, J=17.6 Hz), 6.25 (1H, d, J=1.8 Hz), 6.67
(1H, dd, J=2.7 Hz, J=8.4 Hz), 6.78 (1H, d, J=2.1 Hz),
7.40 (1H, d, J=8.4 Hz), 7.79 (1H, br s). 13C NMR (74.47
MHz) (CDCl3) l CDCl3: 27.7 (q), 38.5 (s), 97.0 (d), 97.9
(d), 109.6 (d), 112.3 (t), 120.9 (d), 123.1 (s), 136.9 (s),
145.0 (s), 146.3 (d), 151.3 (s). IR (NaCl, neat): 3419, 2968,
1628, 1462, 1352, 1228, 1156, 918, 807 cm−1. MS (FAB+):
201 (M+, 100%). HRMS (FAB), calcd for C13H15NO
(M+): 201.1154. Found: 201.1154; (d) 2-(1,1-dimethylal-
lyl)-6-(1,1-dimethylprop-2-ynyloxy)-1H-indole (14). Pale
8. Rousseau, G.; Conia, J. M. Tetrahedron Lett. 1981, 22,
649–652.
9. Nozoe, T.; Takase, K.; Yasunami, M.; Ando, M.; Saito,
H.; Imafuku, K.; Yin, B.-Z.; Honda, M.; Goto, Y.;
Hanaya, T.; Hara, Y.; Yamamoto, H. Bull. Chem. Soc.
Jpn. 1989, 62, 128–142.
1
yellow oil. H NMR (300 MHz) (CDCl3) l CHCl3: 1.49
(6H, s), 1.66 (6H, s), 2.56 (1H, s), 5.15 (2H, m), 6.06 (1H,
dd, J=10.5 Hz, J=17.4 Hz), 6.28 (1H, dd, J=0.6 Hz,
J=2.1 Hz), 6.96 (1H, dd, J=2.1 Hz, J=8.7 Hz), 7.24
(1H, d, J=1.8 Hz), 7.42 (1H, d, J=8.4 Hz), 7.83 (1H, br
10. Sanz-Cervera, J. F.; Glinka, T.; Williams, R. M. Tetra-
hedron 1993, 49, 8471–8482.