9244
T. Yoshimura et al. / Tetrahedron Letters 45 (2004) 9241–9244
Joo, J. M.; Kang, J. W.; Kim, D. S.; Jung, C. K.; Kwak,
H. S.; Park, J. H.; Lee, E.; Hong, C. Y.; Jeong, S. W.;
Jeon, K.; Park, J. H. J. Org. Chem. 2003, 68, 8080–8087.
3. (a) Kang, S. H.; Kang, S. Y.; Kim, C. M.; Choi, H. W.;
Jun, H. S.; Lee, B. M.; Park, C. M.; Jeong, J. W. Angew.
Chem., Int. Ed. 2003, 42, 4779–4782; (b) Kang, S. H.;
Kang, S. Y.; Choi, H. W.; Kim, C. M.; Jun, H. S.; Youn,
J. H. Synthesis 2004, 1102–1114.
4. During this synthetic study, it was revealed that (+)-
lasonolide A is the natural enantiomer by the total
synthesis of Lee and co-workers.2a However, they
reported2b that (À)-lasonolide A was found to be the
biologically active enantiomer and the optical rotation
data for natural lasonolide A in the original report1 is in
error. Therefore, the syntheses of (À)-lasonolide A and its
analogs would be of great significance.
Figure 2. ORTEP drawing of 3 (R = TBDPS).
interesting inversion will be made in our laboratories in
due course.
5. (a) Ohtsuka, M.; Takekawa, Y.; Shishido, K. Tetrahedron
Lett. 1998, 39, 5803–5806; (b) Yamamura, I.; Fujiwara,
Y.; Yamato, T.; Irie, O.; Shishido, K. Tetrahedron Lett.
1997, 38, 4121–4124; (c) Fujiwara, Y.; Yamato, T.; Bando,
T.; Shishido, K. Tetrahedron: Asymmetry 1997, 8, 2793–
2799.
Acknowledgements
We thank Professor Tadashi Nakata (Tokyo University
of Science) for providing us with the 1H NMR spectrum
of 10 and also thank Dr. Masahiko Bando (Otsuka
Pharmaceutical Co., Ltd) for X-ray analysis. This work
was supported financially by the Uehara Memorial
Foundation and by a Grant-in-Aid of Scientific Re-
search (B) (No 14370722) from the Japan Society for
the Promotion of Science. We also thank the Sasakawa
Scientific Research Grant from the Japan Science Soci-
ety for funding to T.Y.
6. Hanessian, S.; Ugolini, A.; Dube, D.; Glamyan, A. Can. J.
Chem. 1984, 62, 2146–2147.
7. Fukui, M.; Okamoto, S.; Sano, T.; Nakata, T.; Oishi, T.
Chem. Pharm. Bull. Jpn. 1990, 38, 2890–2892.
8. Still, W. C. J. Am. Chem. Soc. 1978, 100, 1481–1487.
9. The stereochemistry of 12 was confirmed by the NOE
experiment.
10. Stork, G.; Sher, P. M. J. Am. Chem. Soc. 1986, 108, 303–
304.
11. Tamao, K.; Nagata, K.; Ito, Y.; Maeda, K.; Shiro, M.
Synlett 1994, 257–259.
12. Crystal data of 3: C29H39NO4Si, M = 493.72, monoclinic,
References and notes
˚ ˚
1. Horton, P. A.; Koehn, F. E.; Longley, R. E.; McConnell,
O. J. J. Am. Chem. Soc. 1994, 116, 6015–6016.
space group P21, a = 10.833(1)A, b = 9.862(2)A, c =
˚
3
˚
13.138(1)A, b = 91.039(9)°, V = 1403.4(4)A , Z = 2,
2. (a) Lee, E.; Song, H. Y.; Kang, J. W.; Kim, D. S.; Jung, C.
K.; Joo, J. M. J. Am. Chem. Soc. 2002, 124, 384–385; (b)
Lee, E.; Song, H. Y.; Joo, J. M.; Kang, J. W.; Kim, D. S.;
Jung, C. K.; Hong, C. Y.; Jeong, S. W.; Jeon, K. Bioorg.
Med. Chem. Lett. 2002, 12, 3519–3520; (c) Song, H. Y.;
Dc = 1.168MgmÀ3, F(000) = 532, l(MoKa) = 1.160cmÀ1
.
The final R and wR were 0.037 and 0.042 for 316
parameters. The crystallographic data will be sent on
quoting the CCDC number, CCDC 249373 (e-mail;
deposit@ccdc.cam.ac.uk).