References
1
Gulavita N.
Hori A.
Shimizu Y.
Laszlo P.
Clardy J.
Tetrahedron Lett.
1988,
29:
4381
2
Honda T.
Yamamoto A.
Cui Y.
Tsubuki M.
J. Chem. Soc., Perkin Trans. 1
1992,
531
3
Hallinan KO.
Honda T.
Tetrahedron
1995,
51:
12211
4a
Takano S.
Inomata K.
Sato T.
Takahashi M.
Ogasawara K.
J. Chem. Soc., Chem. Commun.
1990,
290
4b
Hulme AN.
Henry SS.
Meyers AI.
J. Org. Chem.
1995,
60:
1265
4c
Meyers AI.
Schmidt W.
Santiago B.
Heterocycles
1995,
40:
525
4d
Fadel A.
Arzel P.
Tetrahedron: Asymmetry
1995,
6:
893
4e
Node M.
Imazato H.
Kurosaki R.
Kawano Y.
Inoue T.
Nishide K.
Fuji K.
Heterocycles
1996,
42:
811
4f
Shiotani S.
Okada H.
Nakamata K.
Yamamoto T.
Sekino F.
Heterocycles
1996,
43:
1031
4g
Fadel A.
Arzel P.
Tetrahedron: Asymmetry
1997,
8:
371
4h
Shimizu M.
Kamikubo T.
Ogasawara K.
Heterocycles
1997,
46:
21
4i
Tanaka K.
Taniguchi T.
Ogasawara K.
Tetrahedron Lett.
2001,
42:
1049
4j
Tamura O.
Yanagimachi T.
Kobayashi T.
Ishibashi H.
Org. Lett.
2001,
3:
2427
4k
Fuchs JR.
Funk RL.
Org. Lett.
2001,
3:
3923
4l
ElAzab AS.
Taniguchi T.
Ogasawara K.
Heterocycles
2002,
56:
39
4m
Taylor SK.
Ivanovic M.
Simons LJ.
Davis MM.
Tetrahedron: Asymmetry
2003,
14:
743
4n
Kita Y.
Futamura J.
Ohba Y.
Sawama Y.
Genesh JK.
Fujioka H.
J. Org. Chem.
2003,
68:
5917
4o
Zhai H.
Luo S.
Ye C.
Ma Y.
J. Org. Chem.
2003,
68:
8268
4p
Tamura O.
Yanagimachi T.
Ishibashi H.
Tetrahedron: Asymmetry
2003,
14:
3033
4q Synthesis of (+)-aphanorphine, see: Takano S.
Inomata K.
Sato T.
Ogasawara K.
J. Chem. Soc., Chem. Commun.
1989,
1591
5
Honda T.
Ishikawa F.
Chem. Commun.
1999,
1065
6a
Honda T.
Kimura M.
Org. Lett.
2000,
2:
3925
6b
Katoh M.
Matsune R.
Nagase H.
Honda T.
Tetrahedron Lett.
2004,
45:
6221
6c
Honda T.
Takahashi R.
Namiki H.
J. Org. Chem.
2005,
70:
499
6d
Katoh M.
Mizutani H.
Honda T.
Tetrahedron Lett.
2005,
46:
5161
7a
Katritzky AR.
Lan X.
Yang JZ.
Denisko OV.
Chem. Rev.
1998,
98:
409
7b
Katritzky AR.
Cobo-Domingo J.
Yang B.
Steel PJ.
Tetrahedron: Asymmetry
1999,
10:
255
7c
Koepler O.
Laschat S.
Baro A.
Fischer P.
Miehlich B.
Hotfilder M.
le Viseur C.
Eur. J. Org. Chem.
2004,
3611
8
Jurczak J.
Gryko D.
Kobrzycka E.
Gruza H.
Prokopowicz P.
Tetrahedron
1998,
54:
6051
9
Preparation and Spectroscopic Data of Compound 9.
To a stirred solution of 8 (1.00 g, 2.74 mmol) in THF (15 mL) was added a solution of SmI2 (0.2 M in THF, 68.5 mL, 13.7 mmol) containing HMPA (2.38 mL, 13.7 mmol) and MeOH (0.28 mL, 6.85 mmol) at 0 °C. The solution was gradually warmed up to r.t., and stirred overnight. To this solution were added excess of sat. NaHCO3 solution, Et2O and Celite. After removal of insoluble materials by filtration through Celite pad, the filtrate was extracted with EtOAc. The extract was washed with brine and dried over Na2SO4. Evaporation of the solvent gave a residue, which was subjected to column chromatography on silica gel. Elution with EtOAc-hexane (1:2) gave 9 (541 mg, 59%) as a colorless solid; mp 97-99 °C; [α]D
28 -11.7 (c 0.45, CHCl3). 1H NMR (270 MHz, CDCl3): δ = 7.05 (d, J = 8.9 Hz, 1 H), 6.72-6.78 (m, 2 H), 5.90 (br s, 1 H), 3.83 (d, J = 15.3 Hz, 1 H), 3.78 (s, 3 H), 3.72 (d, J = 15.3 Hz, 1 H), 3.55-3.67 (m, 2 H), 3.41-3.55 (m, 1 H), 2.99 (dd, J = 8.9, 15.1 Hz, 1 H), 2.90 (dd, J = 4.5, 15.1 Hz, 1 H), 0.90 (s, 9 H), 0.07 (s, 6 H). 13C NMR (68 MHz, CDCl3): δ = -5.4, 18.1, 25.7, 33.1, 42.7, 55.2, 55.3, 66.3, 112.7, 114.7, 128.1, 129.9, 134.5, 158.6, 170.8. IR (KBr): 3220, 2950, 2930, 2855, 1666, 1565, 1260, 1110, 840, 780 cm-1. MS (EI): m/z = 335 [M+]. Anal. Calcd for C18H29NO3Si: C, 64.44; H, 8.71; N, 4.17. Found: C, 64.53; H, 8.78; N, 4.16.
10 Compound 13: mp 144-145 °C; [α]D
25 +21.9 (c 0.71, CHCl3). 1H NMR (270 MHz, CDCl3): δ = 6.99 (d, J = 8.4 Hz, 1 H), 6.84 (d, J = 2.6 Hz, 1 H), 6.73 (dd, J = 2.6, 8.4 Hz, 1 H), 3.84 (dt, J = 2.5, 5.3 Hz, 1 H), 3.78 (s, 3 H), 2.91-2.97 (m, 2 H), 2.83 (s, 3 H), 2.18 (ddd, J = 0.9, 5.3, 10.7 Hz, 1 H), 2.02 (d, J = 10.7 Hz, 1 H), 1.55 (s, 3 H). 13C NMR (68 MHz, CDCl3): δ = 17.4, 27.5, 29.9, 40.7, 45.1, 54.9, 55.2, 110.0, 112.7, 124.4, 130.6, 141.4, 158.1, 177.0. IR (KBr): 2960, 1686, 1490, 1431, 1286, 1042 cm-1. MS (EI): m/z = 231 [M+]. Anal. Calcd for C14H17NO2: C, 72.70; H, 7.41; N, 6.06. Found: C, 72.79; H, 7.53; N, 6.08.