C. F. Morrison, D. J. Burnell / Tetrahedron Letters 42 (2001) 7367–7369
7369
(4C, 1), 114.9 (0), 106.0 (1), 97.9 (1), 65.3 (2), 56.5 (3),
27.3 (3C, 3), 20.0 (0).
References
9. Data for 8 (R=TBDPS): mp 82–84 °C; IR (Nujol) 3380
1. Ozaki, Y.; Imaizumi, K.; Okamura, K.; Morozumi, M.;
Hosoya, A.; Kim, S.-W. Chem. Pharm. Bull. 1996, 44,
1785–1789.
(broad), 1712, 1620 cm−1 1H NMR (CD3COCD3): l
;
10.22 (1H, s), 7.81–7.71 (4H, m), 7.51–7.37 (6H, m), 6.55
(1H, d, J=2.1 Hz), 6.39 (1H, d, J=2.1 Hz), 5.13 (2H, s,
irradiation of this signal led to NOE enhancements at l
10.22 and 6.55), 3.85 (3H, s), 3.25 (1H, s, OH), 1.07 (9H,
s); 13C NMR (CD3COCD3): l 194.6 (1), 167.4 (0), 167.3
(0), 147.0 (0), 136.3 (4C, 1), 135.6 (2C, 0), 130.9 (2C, 1),
128.8 (4C, 1), 112.8 (0), 108.5 (1), 100.5 (1), 63.9 (2), 56.2
(3), 27.2 (3C, 3), 19.8 (0).
2. Harland, P. A.; Hodge, P. Synthesis 1982, 223.
3. (a) Torisawa, Y.; Satoh, K.; Ikegami, S. Heterocycles
1989, 28, 729–732; (b) Carreira, E. M.; Lee, W.; Singer,
R. A. J. Am. Chem. Soc. 1995, 117, 3649–3650; (c)
Marshall, J. A.; Garofalo, A. W. J. Org. Chem. 1996, 61,
8732–8738; (d) Singer, R. A.; Carreira, E. M. Tetrahedron
Lett. 1997, 38, 927–930; (e) Wipf, P.; Rahman, L. T.;
Rector, S. R. J. Org. Chem. 1998, 63, 7132–7133; (f)
Singer, R. A.; Shepard, M. S.; Carreira, E. M. Tetra-
hedron 1998, 54, 7025–7032.
4. Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
5. PCC and PDC gave a 7% yield of 3. Other researchers
have used manganese dioxide, barium manganate and the
Swern protocol. See: (a) Motto, M. G.; Sheves, M.;
Tsujimoto, K.; Balogh-Nair, V.; Nakanishi, K. J. Am.
Chem. Soc. 1980, 102, 7947–7949; (b) Garigipati, R. S.;
Freyer, A. J.; Whittle, R. W.; Weinreb, S. M. J. Am.
Chem. Soc. 1984, 106, 7861–7867; (c) Irie, H.; Mat-
sumoto, K.; Kitagawa, T.; Zhang, Y. Chem. Pharm. Bull.
1990, 38, 1451–1461; (d) Toshima, H.; Aramaki, H.;
Ichihara, A. Tetrahedron Lett. 1999, 40, 3587–3590. In
contrast with other authors, we did not find 3 to be
particularly volatile or unstable.
1
10. Data for 7 (from the mixture with 5): H NMR (CDCl3):
l 4.99 (1H, m), 4.15 (1H, d, J=1.8 Hz), 3.52 (3H, s), 2.08
(2H, d, J=1.2 Hz), 1.05 (6H, s), 0.23 (9H, s).
11. Truce, W. E.; Roberts, F. E. J. Org. Chem. 1963, 28,
961–964.
12. Hatch, R. P.; Shringarpure, J.; Weinreb, S. M. J. Org.
Chem. 1978, 43, 4172–4177.
13. Data for 2: mp 92–93°C; IR (Nujol) 3400 (br), 1605 cm−1
;
1H NMR (CD3COCD3): l 6.86 (1H, d, J=2.4 Hz), 6.54
(1H, s), 6.48 (1H, d, J=2.4 Hz), 5.07 (2H, d, J=6.0 Hz),
4.10 (1H, t, J=6.0 Hz, OH), 3.84 (3H, s), 3.80 (3H, s),
3.56 (2H, m), 3.33 (2H, m); 13C NMR (CD3COCD3): l
157.0 (0), 146.3 (0), 127.0 (0), 113.0 (0), 106.1 (1), 98.0
(1), 61.5 (2), 56.5 (3), 55.6 (3), 47.3 (1), 40.9 (2C, 2).
14. Burkett, H.; Schubert, W. M.; Schultz, F.; Murphy, R.
B.; Talbott, R. J. Am. Chem. Soc. 1959, 81, 3923–3929.
15. (a) Schubert, W. M.; Burkett, H. J. Am. Chem. Soc. 1956,
78, 64–68; (b) Schubert, W. M.; Myhre, P. C. J. Am.
Chem. Soc. 1958, 80, 1755–1761; (c) Clark, J.; Parvizi, B.;
Southon, I. W. Chem. Ind. (London) 1974, 661–662.
16. Schubert, W. M.; Kintner, R. R. In The Chemistry of the
Carbonyl Group; Patai, S., Ed.; Interscience: New York,
1966; pp. 695–760.
6. Danishefsky, S.; Kitahara, J. J. Am. Chem. Soc. 1974, 96,
7807–7808.
7. The enolate of 3-methoxy-5,5-dimethylcyclohex-2-en-1-
one was trapped by TMS-Cl at −78°C to give 5 in 82%
yield. See: Girard, C.; Conia, J. M. J. Chem. Res. (M)
1
1978, 2351. Data for 5: bp 50–53°C/0.4 mmHg; H NMR
(CDCl3): l 4.72 (1H, narrow m), 4.38 (1H, d, J=1.5 Hz),
3.58 (3H, s), 2.09 (2H, d, J=0.9 Hz), 1.02 (6H, s), 0.20
(9H, s); 13C NMR (C6D6): l 160.6, 148.8, 107.2, 94.6,
54.7, 43.0, 33.0, 29.4, 0.7.
17. (a) Tsuji, J.; Ohno, K. Tetrahedron Lett. 1965, 3969–
3971; (b) Ohno, K.; Tsuji, J. J. Am. Chem. Soc. 1968, 90,
99–107; (c) Baird, M. C.; Nyman, C. J.; Wilkinson, G. J.
Chem. Soc. A 1968, 348–351; (d) Tsuji, J.; Ohno, K.
Synthesis 1969, 1, 157–169; (e) Rylander, P. N. Organic
Synthesis with Noble Metal Catalysts; Academic Press:
New York, 1973; pp. 80–87 and 260–267.
18. Ito, S.; Morita, N.; Asao, T. Bull. Chem. Soc. Jpn. 1999,
72, 2543–2548.
19. Smith, M. B.; March, J. March’s Advanced Organic
Chemistry: Reactions, Mechanism and Structure, 5th ed.;
John Wiley & Sons: New York, 2001; pp. 732–734.
8. Data for 6 (R=TBDPS): mp 181–182°C; IR (Nujol) 3400
(br), 1713, 1588 cm−1 1H NMR (CD3COCD3): l 10.30
;
(1H, s), 7.75–7.72 (4H, m), 7.50–7.40 (6H, m), 7.31 (1H,
narrow m), 6.53 (1H, d, J=2.0 Hz), 5.16 (2H, s, irradia-
tion of this signal led to NOE enhancements at l 10.30
and 7.31), 3.92 (3H, s), 3.78 (1H, OH), 1.12 (9H, s); 13C
NMR (CD3COCD3): l 189.3 (1), 166.7 (0), 165.0 (0),
148.9 (0), 136.2 (4C, 1), 134.2 (2C, 0), 130.8 (2C, 1), 128.8