4396
S. Kowashi et al. / Tetrahedron Letters 45 (2004) 4393–4396
3. Evans, D. A.; Rieger, D. L.; Jones, T. K.; Kaldor, S. W.
J. Org. Chem. 1990, 55, 6260.
Acknowledgements
4. (a) Hale, K. J.; Manaviazar, S.; Peak, S. A. Tetrahedron
Lett. 1994, 35, 425; (b) Hale, K. J.; Cai, J. Tetrahedron Lett.
1996, 37, 4233.
5. The enantiomer excess (89% ee) of the AD reaction was
determined by the 1H NMR analysis of the (R)-MTPA
ester, produced by esterification of a precursor of 5.4
6. Blakemore, P. R.; Cole, W. J.; Kocienski, P. J.; Morley, A.
This work was supported by Grant-in-Aid for the 21st
Century COE program ‘Keio Life Conjugate Chemis-
try’, as well as Scientific Research C from the Ministry
of Education, Culture, Sports, Science, and Technology,
Japan. The authors are grateful to the COE program for
financial support to T.O.
Synlett 1998, 2 6.
26
D
7. 2: ½a +31.3 (c 0.0083, CHCl3); IR (film) m 1757, 1460,
968 cmÀ1
;
1H NMR (400 MHz, CDCl3) d 0.81 (3H, t,
References and notes
J ¼ 7:3 Hz), 0.82(3H, t,
J ¼ 7:3 Hz), 0.96 (3H, t,
1. (a) Patil, A. D.; Freyer, A. J.; Bean, M. F.; Carte, B. K.;
Westley, J. W.; Johnson, R. K. Tetrahedron 1996, 52, 377;
(b) Schmidt, E. W.; Faulkner, D. J. Tetrahedron Lett. 1996,
37, 6681; (c) Breakman, J. C.; Daloze, D.; De Groote, S.;
Fernandes, J. B.; Van Soest, R. W. M. J. Nat. Prod. 1998,
61, 1038; (d) Cafieri, F.; Fattorusso, E.; Taglialatela-
Scafati, O. Tetrahedron 1999, 55, 13831;
J ¼ 7:3 Hz), 1.15 (3H, t, J ¼ 7:3 Hz), 1.18 (2H, m), 1.26–
1.36 (4H, complex), 1.67–1.75 (3H, complex), 1.79 (2H,
complex), 2.00 (2H, complex), 2.30 (2H, dq, J ¼ 7:3,
1.5 Hz), 5.03 (1H, dd, J ¼ 15:1, 8.8 Hz), 5.36 (1H, dt,
J ¼ 15:1, 6.4 Hz), 6.82(1H, m); 13C NMR (100 MHz,
CDCl3) d 8.4, 12.2, 12.6, 14.8, 19.1, 21.7, 26.2, 28.7, 30.6,
35.6, 37.3, 44.7, 89.8, 132.8, 133.4, 136.3, 150.5, 173.9.
HRMS (EI) calcd for C18H30O2 (Mþ) 278.2244, found: m=z
(e) Gochfeld, D. J.; Hamann, M. T. J. Nat. Prod. 2001, 64,
1477; (f) Jimenez, M. D. S.; Garzon, S. P.; Rodriguez, A. D.
J. Nat. Prod. 2003, 66, 655.
278.2246.
20
D
8. 14: ½a )25.3 (c 0.0083, CHCl3); IR (film) m 1755, 1460,
968 cmÀ1
;
1H NMR (400 MHz, CDCl3) d 0.80 (3H, t,
2. (a) Paddon-Jones, G. C.; Hungerford, N. L.; Hayes, P.;
Kitching, W. Org. Lett. 1999, 1, 1905; (b) Bittner, C.;
Burgo, A.; Murphy, P. J.; Sung, C. H.; Thornhill, A. J.
Tetrahedron Lett. 1999, 40, 3455; (c) Semmelhack, M. F.;
Shanmugam, P. Tetrahedron Lett. 2000, 41, 3567; (d) Hui,
C. W.; Lee, H. K.; Wong, H. N. C. Tetrahedron Lett. 2002,
43, 123; (e) Yao, G.; Steliou, K. Org. Lett. 2002, 4, 485; (f)
Lee, H. K.; Wong, H. N. C. Chem. Commun. 2002, 2114;
(g) Hayes, P. Y.; Kitching, W. J. Am. Chem. Soc. 2002, 124,
9718; (h) Hayes, P. Y.; Kitching, W. Heterocycles 2004, 62,
173.
J ¼ 7:3 Hz), 0.82(3H, t,
J ¼ 7:3 Hz), 0.96 (3H, t,
J ¼ 7:3 Hz), 1.15 (3H, t, J ¼ 7:3 Hz), 1.16 (4H, complex),
1.25 (1H, m), 1.32 (1H, m), 1.60 (1H, m), 1.68–1.85 (4H,
complex), 1.99 (2H, complex), 2.29 (2H, dq, J ¼ 7:3,
1.5 Hz), 5.02(1H, dd, J ¼ 15:1, 8.8 Hz), 5.35 (1H, dt,
J ¼ 15:1, 6.4 Hz), 6.83 (1H, t, J ¼ 1:5 Hz); 13C NMR
(100 MHz, CDCl3) d 8.4, 12.2, 12.6, 14.8, 19.1, 21.8, 26.2,
28.8, 30.5, 35.6, 37.4, 44.9, 89.8, 132.8, 133.4, 136.2, 150.6,
173.9. HRMS (EI) calcd for C18H30O2 (Mþ) 278.2244,
found: m=z 278.2234.