4174
F. Yokokawa et al. / Tetrahedron Letters 42 (2001) 4171–4174
1
58% yield. The H and 13C NMR spectra as well as the
specific rotation of our synthetic lyngbyabellin A (1)
were completely identical with those published for the
natural product (Scheme 5).
Anzai, A.; Ando, A.; Shioiri, T. Synlett 1998, 35–36.
6. Takuma, S.; Hamada, Y.; Shioiri, T. Chem. Pharm. Bull.
1982, 30, 3147–3153 and references cited therein.
7. Fehrentz, J.-A.; Castro, B. Synthesis 1983, 676–678.
8. (a) Hashimoto, N.; Aoyama, T.; Shioiri, T. Chem.
Pharm. Bull. 1981, 29, 1475–1478; (b) Shioiri, T.;
Aoyama, T. In Encyclopedia of Reagents for Organic
Synthesis; Paquette, L. A., Ed.; John Wiley & Sons:
Chichester, 1985; Vol. 7, p. 5248.
In summary, we have developed an efficient and con-
vergent strategy for the total synthesis of the struc-
turally and biologically attractive lyngbyabellin A (1).
Application of this strategy to the synthesis of lyngbya-
bellin B2 is currently underway in our laboratory.
9. Raman, P.; Razavi, H.; Kelly, J. W. Org. Lett. 2000, 2,
3289–3292.
10. Williams, D. R.; Lowder, P. D.; Gu, Y.-G.; Brooks, D.
A. Tetrahedron Lett. 1997, 38, 331–334.
Acknowledgements
11. Kolb, H. C.; VanNieuwenhze, M. S.; Sharpless, K. B.
Chem. Rev. 1994, 94, 2483–2547.
12. The ee was determined by chiral HPLC on a ChiralPak
AS column (hexane:isopropanol=50:1; flow rate=1.0
mL/min).
13. (a) Kiyooka, S.-I.; Kaneko, Y.; Komura, M.; Matsuo,
H.; Nakano, M. J. Org. Chem. 1991, 56, 2276–2278; (b)
Kiyooka, S.-I. J. Synth. Org. Chem. Jpn. 1997, 55, 313–
324. See also: (c) Yokokawa, F.; Izumi, K.; Omata, J.;
Shioiri, T. Tetrahedron 2000, 56, 3027–3034.
14. The ee was determined by 1H NMR analysis in the
presence of the chiral shift reagent Eu(hfc)3.
15. Ohtani, I.; Kusumi, T.; Kashman, Y.; Kakisawa, H. J.
Am. Chem. Soc. 1991, 113, 4092–4096.
This work was financially supported in part by a Grant-
in-Aid for Research at Nagoya City University (to
F.Y.), the Uehara Memorial Foundation (to F.Y.), and
Grants-in-Aid from the Ministry of Education, Science,
Sports and Culture, Japan.
References
1. Luesch, H.; Yoshida, W. Y.; Moore, R. E.; Paul, V. J.;
Mooberry, S. L. J. Nat. Prod. 2000, 63, 611–615.
2. An analogue of 1 was recently isolated and named lyng-
byabellin B, see: (a) Luesch, H.; Yoshida, W. Y.; Moore,
R. E.; Paul, V. J. J. Nat. Prod. 2000, 63, 1437–1439; (b)
Milligan, K.; Marquez, B. L.; Williamson, R. T.; Ger-
wick, W. H. J. Nat. Prod. 2000, 63, 1440–1443.
16. Boden, E. P.; Keck, G. E. J. Org. Chem. 1985, 50,
2394–2395.
17. Shioiri, T.; Ninomiya, K.; Yamada, S. J. Am. Chem. Soc.
1972, 94, 6203–6205.
3. Sone, H.; Kondo, T.; Kiryu, M.; Ishiwata, H.; Ojika, M.;
18. In place of DPPA and NaHCO3, FDPP19 and i-Pr2NEt
also produced the macrocycle 1, but its yield was lower
(25%).
Yamada, K. J. Org. Chem. 1995, 60, 4774–4781.
4. (a) Sugiyama, H.; Yokokawa, F.; Shioiri, T. Org. Lett.
2000, 2, 2149–2152; (b) Fujiwara, H.; Tojiki, K.;
Yokokawa, F.; Shioiri, T. Pept. Sci. 1999 2000, 9–12; (c)
Yokokawa, F.; Sameshima, H.; Shioiri, T. Pept. Sci. 2000
2001, 55–58; (d) Yokokawa, F.; Sameshima, H.; Shioiri,
T. Synlett, in press.
5. (a) Hamada, Y.; Shibata, M.; Sugiura, T.; Kato, S.;
Shioiri, T. J. Org. Chem. 1987, 52, 1252–1255; (b)
Aoyama, T.; Sonoda, N.; Yamauchi, M.; Toriyama, K.;
19. (a) Chen, S.; Xu, J. Tetrahedron Lett. 1991, 32, 6711–
6714; (b) Dudash, Jr., J.; Jiang, J.; Mayer, S. C.; Joullie,
M. M. Synth. Commun. 1993, 23, 349–356; (c) Deng, J.;
Hamada, Y.; Shioiri, T.; Matsunaga, S.; Fusetani, N.
Angew. Chem., Int. Ed. Engl. 1994, 33, 1729–1731; (d)
Deng, J.; Hamada, Y.; Shioiri, T. Synthesis 1998, 627–
638.
.