T. Terauchi et al. / Tetrahedron Letters 44 (2003) 7741–7745
7745
16. Kary, P. D.; Roberts, S. M.; Watson, D. J. Tetrahedron:
Asymmetry 1999, 10, 213–216 and references cited
therein.
17. Fernandez-Megia, E.; Gourlaouen, N.; Ley, S. V.; Row-
lands, G. J. Synlett 1998, 991–994.
References
1. (a) Kobayashi, M.; Aoki, S.; Sakai, H.; Kawazoe, K.;
Kihara, N.; Sasaki, T.; Kitagawa, I. Tetrahedron Lett.
1993, 34, 2795–2798; (b) Pettit, G. R.; Cichacz, Z. A.;
Gao, F.; Herald, C. L.; Boyd, M. R.; Schmidt, J. M.;
Hooper, J. N. A. J. Org. Chem. 1993, 58, 1302–1304; (c)
Fusetani, N.; Shinoda, K.; Matsunaga, S. J. Am. Chem.
Soc. 1993, 115, 3977–3981.
2. (a) Evans, D. A.; Coleman, P. J.; Dias, L. C. Angew.
Chem., Int. Ed. Engl. 1997, 36, 2738–2741; (b) Evans, D.
A.; Trotter, B. W.; Coˆte´, B.; Coleman, P. J. Angew.
Chem., Int. Ed. Engl. 1997, 36, 2741–2744; (c) Evans, D.
A.; Trotter, B. W.; Coˆte´, B.; Coleman, P. J.; Dias, L. C.;
Tyler, A. N. Angew. Chem., Int. Ed. Engl. 1997, 36,
2744–2747; (d) Evans, D. A.; Trotter, B. W.; Coleman, P.
J.; Coˆte´, B.; Dias, L. C.; Rajapakse, H. A.; Tyler, A. N.
Tetrahedron 1999, 55, 8671–8726.
3. (a) Guo, J.; Duffy, K. J.; Stevens, K. L.; Dalko, P. I.;
Roth, R. M.; Hayward, M. M.; Kishi, Y. Angew. Chem.,
Int. Ed. 1998, 37, 187–192; (b) Hayward, M. M.; Roth,
R. M.; Duffy, K. J.; Dalko, P. I.; Stevens, K. L.; Guo, J.;
Kishi, Y. Angew. Chem., Int. Ed. 1998, 37, 192–196.
4. (a) Smith, A. B., III; Doughty, V. A.; Lin, Q.; Zhuang,
L.; McBriar, M. D.; Boldi, A. M.; Moser, W. H.;
Murase, N.; Nakayama, K.; Sobukawa, M. Angew.
Chem., Int. Ed. 2001, 40, 191–195; (b) Smith, A. B., III;
Lin, Q.; Doughty, V. A.; Zhuang, L.; McBriar, M. D.;
Kerns, J. K.; Brook, C. S.; Murase, N.; Nakayama, K.
Angew. Chem., Int. Ed. 2001, 40, 196–199; (c) Smith, A.
B., III; Zhu, W.; Shirakami, S.; Sfouggatakis, C.;
Doughty, V. A.; Bennett, C. S.; Sakamoto, Y. Org. Lett.
2003, 5, 761–764 and references cited therein.
5. Paterson, I.; Chen, D. Y.-K.; Coster, M. J.; Acena, J. L.;
Bach, J.; Gibson, K. R.; Keown, L. E.; Oballa, R. M.;
Trieselmann, T.; Wallace, D. J.; Hodgson, A. P.; Nor-
cross, R. D. Angew. Chem., Int. Ed. 2001, 40, 4055–4060
and references cited therein.
6. Crimmins, M. T.; Katz, J. D.; Washburn, D. G.; Allwein,
S. P.; McAtee, L. F. J. Am. Chem. Soc. 2002, 124,
5661–5663 and references cited therein.
7. (a) Cho, I. H.; Paquette, L. A. Heterocycles 2002, 58,
43–46 and references cited therein; (b) Zuev, D.;
Paquette, L. A. Org. Lett. 2000, 2, 679–682.
8. Holson, E. B.; Roush, W. R. Org. Lett. 2002, 4, 3719–
3722 and references cited therein.
18. Zemribo, R.; Mead, K. T. Tetrahedron Lett. 1998, 39,
3891–3894 and references cited therein.
19. (a) Terauchi, T.; Nakata, M. Tetrahedron Lett. 1998, 39,
3795–3798; (b) Terauchi, T.; Terauchi, T.; Sato, I.;
Tsukada, T.; Kanoh, N.; Nakata, M. Tetrahedron Lett.
2000, 41, 2649–2653; (c) Terauchi, T.; Morita, M.; Kimi-
jima, K.; Nakamura, Y.; Hayashi, G.; Tanaka, T.;
Kanoh, N.; Nakata, M. Tetrahedron Lett. 2001, 42,
5505–5508.
20. The C23 stereocenter is reported to be epimerized to the
natural congener in the final stage of the synthesis. See
Ref. 4b.
21. (a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48,
4155–4156; (b) Dess, D. B.; Martin, J. C. J. Am. Chem.
Soc. 1991, 113, 7277–7287.
22. (a) Mukaiyama, T.; Banno, K.; Narasaka, K. J. Am.
Chem. Soc. 1974, 96, 7503–7509; (b) Evans, D. A.; Dart,
M. J.; Duffy, J. L.; Yang, M. G. J. Am. Chem. Soc. 1996,
118, 4322–4343.
23. The model aldehydes 8 and 9 were prepared from methyl
(S)-3-hydroxy-2-methylpropionate as follows: (a) TrCl,
Et3N, DMAP, CH2Cl2, rt; (b) DIBALH, CH2Cl2–hexane,
−78°C; (c) EtMgBr, ether, rt; (d) CSA, MeOH, rt, separa-
tion of two diastereomers, which were identical with
authentic samples by comparison of their optical rota-
tions and 1H NMR spectra, see: Fujisawa, T.; Tajima,
K.; Sato, T. Chem. Lett. 1984, 1669–1672; Kayano, A.;
Akazome, M.; Fujita, M.; Ogura, K. Tetrahedron 1997,
53, 12101–12114; (e) p-MeOPhCH(OMe)2, CSA, CH2Cl2,
rt; (f) DIBALH, CH2Cl2–hexane, −40°C; (g) Dess–Martin
oxidation.
24. Kiyooka, S.; Kuroda, H.; Shimasaki, Y. Tetrahedron
Lett. 1986, 27, 3009–3012.
25. (a) Rychnovsky, S. D.; Skalitzky, D. J. Tetrahedron Lett.
1990, 31, 945–948; (b) Rychnovsky, S. D.; Rogers, B. N.;
Yang, G. J. Org. Chem. 1993, 58, 3511–3515; (c) Rych-
novsky, S. D.; Yang, G.; Powers, J. P. J. Org. Chem.
1993, 58, 5251–5255; (d) Rychnovsky, S. D.; Rogers, B.
N.; Richardson, T. I. Acc. Chem. Res. 1998, 31, 9–17.
26. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J.
Am. Chem. Soc. 1991, 113, 4092–4096.
27. Since it was difficult to determine the stereochemistry at
the newly formed carbon centers (C14, C15), it was
tentatively assigned as depicted, depending on the model
studies as described above. Moreover, the fact that the
coupling constants (J=8.8, 2.4 Hz) around the C15 stereo-
center of acetate 24 (R=Ac) were close to those (J=9.2,
2.8 Hz) of the Paquette’s compound supports the assign-
ment. See Ref. 7b.
9. Wallace, G. A.; Scott, R. W.; Heathcock, C. H. J. Org.
Chem. 2000, 65, 4145–4152 and references cited therein.
10. Lemaire-Audoire, S.; Vogel, P. J. Org. Chem. 2000, 65,
3346–3356 and references cited therein.
11. Samadi, M.; Munoz-Letelier, C.; Poigny, S.; Guyot, M.
Tetrahedron Lett. 2000, 41, 3349–3353.
12. Uckun, F. M.; Mao, C.; Vassilev, A. O.; Huang, H.; Jan,
S.-T. Bioorg. Med. Chem. Lett. 2000, 10, 541–545.
13. Anderson, J. C.; MaDermott, B. P.; Griffin, E. J. Tetra-
hedron 2000, 56, 8747–8767 and references cited therein.
14. Barrett, A. G. M.; Braddock, D. C.; de Koning, P. D.;
White, A. J. P.; Williams, D. J. J. Org. Chem. 2000, 65,
375–380.
28. Other groups also experienced a similar epimerization in
their synthetic studies. See Refs. 3a and 4a.
29. Paquette et al. reported that they succeeded in the
methylenation of the C13 ketone with Tebbe reagent
albeit in low yield. See Ref. 7b.
30. Terauchi, T.; Tanaka, T.; Terauchi, T.; Morita, M.;
Kimijima, K.; Sato, I.; Shoji, W.; Nakamura, Y.;
Tsukada, T.; Tsunoda, T.; Hayashi, G.; Kanoh, N.;
Nakata, M. Tetrahedron Lett. 2003, 44, 7747–7751.
15. Dunkel, R.; Treu, J.; Hoffmann, H. M. R. Tetrahedron:
Asymmetry 1999, 10, 1539–1549.