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the reaction mixture was warmed slowly to room temperature and was stirred
References and notes
at room temperature for 3 h. The reaction mixture was concentrated to give the
crude residue. To a solution of the crude residue in MeOH (6 mL) was added
DABCO (44.8 mg, 0.4 mmol) and the reaction mixture was stirred at room
temperature for 8 h. The reaction mixture was concentrated to give the crude
residue which was purified by silica gel column chromatography to give the
carbonate 12c-syn (354.5 mg, 1.50 mmol) and 12c-anti (70.9 mg, 0.30 mmol) in
88% yield.
1. Silveira, C. C.; Braga, A. L.; Kaufman, T. S.; Lenardao, E. J. Tetrahedron 2004, 60,
8295–8328. and references cited therein.
2. Taber, D. F.; Neubert, T. D.; Rheingold, A. L. J. Am. Chem. Soc. 2002, 124, 12416–
12417.
3. (a) McKervey, M. A.; Tuladhar, S. M.; Twohig, M. F. Chem. Commun. 1984, 129–
130; (b) Kennedy, M.; McKervey, M. A.; Maguire, A. R.; Tuladhar, S. M.; Twohig,
M. F. J. Chem. Soc., Perkin Trans. 1 1990, 1047–1054.
4. Moriarty, R. M.; May, E. J.; Prakash, O. Tetrahedron Lett. 1997, 38, 4333–4336.
5. (a) Cordi, A. A.; Lacoste, J.-M.; Descombes, J.-J.; Courchay, C.; Vanhoutee, P. M. J.
Med. Chem. 1995, 38, 4056–4069; (b) Brown, E.; Ragault, M. Tetrahedron 1979,
35, 911–927.
6. (a) Oikawa, Y.; Yonemitsu, O. Tetrahedron 1974, 30, 2653–2660; (b) Makhey, D.;
Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. Bioorg. Med. Chem. 2000, 8, 1171–1182; (c)
Oikawa, Y.; Yonemitsu, O. Tetrahedron Lett. 1972, 15, 3393–3396.
7. Hon, Y. S.; Kao, C. Y. Tetrahedron Lett. 2009, 50, 748–751.
8. (a) Jeffrey, T. Chem. Commun. 1984, 1287–1289; (b) Battistuzzi, G.; Cacchi, S.;
Fabrizi, G. Org. Lett. 2003, 5, 777–780; (c) Hashizume, H.; Ito, H.; Yamada, K.;
Nagashima, H.; Kanao, M.; Tomoda, H.; Sunazuka, T.; Kumagai, H.; Omura, S.
Chem. Pharm. Bull. 1994, 42, 512–520; (d) Caló, V.; Nacci, A.; Monopoli, A.;
Spinelli, M. Eur. J. Org. Chem. 2003, 1382–1385.
9. General procedure for the preparation of cyclic carbonate (12c): A two-necked
flask fitted with a glass tube to admit ozone, a CaCl2 drying tube, and a
magnetic stirring bar was charged with alkene 11c (479.2 mg, 2.0 mmol) in
CH2Cl2 (10 mL). The flask was cooled to ꢀ78 °C and O3 was bubbled through
the solution. When the solution turned blue, ozone addition was stopped and
N2 was passed through the solution until the blue color was discharged. To the
resulting ozonide in CH2Cl2 was added Ph3P (419.7 mg, 1.6 mmol) at ꢀ78 °C,
10. (a) Hon, Y. S.; Wang, Y. C. Tetrahedron Lett. 2005, 46, 1365–1368; (b) Hon, Y. S.;
Wang, Y. C.; Wu, K. J. J. Chin. Chem. Soc. 2008, 55, 896–914; (c) Waszkuc, W.;
Janecki, T.; Bodalski, R. Synthesis 1984, 1025–1027.
11. General procedure for the preparation of 2-tetralone (13b): To a solution of 4-
methoxy-5-phenethyl-1,3-dioxolan-2-one (12b) (62 mg, 0.29 mmol) in 5 mL of
CH2Cl2, TiCl4 (0.58 mmol, 0.58 mL, 1 M in CH2Cl2) was added dropwise at
ꢀ78 °C over a period of 5 min. The reaction mixture was warmed slowly to rt in
a period of 5 h. The reaction mixture was quenched with saturated aqueous
NaHCO3 and was extracted with CH2Cl2. The organic layer was dried over
MgSO4, concentrated, and chromatographed on silica gel column to give 2-
teralone (13b, 35.2 mg) as a pale yellow oil in 83% yield. TLC Rf = 0.57 (hexane/
EtOAc = 6:1); 1H NMR (CDCl3, 400 MHz) d 2.53–2.57 (t, J = 6.6 Hz, 2H), 3.05–
3.08 (t, J = 6.6 Hz, 2H), 3.59 (s, 2H), 7.12–7.23 (m, 4H); 13C NMR (CDCl3,
100 MHz) d 28.3 (2°), 38.1 (2°), 45.0 (2°), 126.8 (3°), 126.8 (3°), 127.5 (3°), 128.2
(3°), 133.2 (4°), 136.7 (4°), 210.6 (4°); IR (KBr, neat) 3023, 2952, 2849, 1716,
1456, 1238, 749 cmꢀ1; MS m/z (relative intensity): 147 (M++1, 1), 146 (M+, 71),
117 (28), 104 (100), 103 (15), 91 (14), 78 (12); HRMS calcd for C10H10O:
146.0732. Found: 146.0731.
12. Wyrick, S. D.; Booth, R. G.; Myers, A. M.; Owens, C. E.; Kula, N. S.; Baldessarini,
R. J.; McPhai1, A. T.; Mailman, R. B. J. Med. Chem. 1993, 36, 2542–2551.