Acad. Sci. U.S.A., 1989, 86, 4695. (e) P. A. Cerutti, Science, 1985, 227, 375.
2. (a) Carazostatin for the isolation: S. Kato, H. Kawai, T. Kawasaki, Y. Toda, T. Urata, and Y.
Hayakawa, J. Antibiot., 1989, 42, 1879. For its bioactivity: M. Iwatsuki, E. Niki, S. Kato,
and K. Nishikori, Chem. Lett., 1992, 1735: S. Kato, T. Kawasaki, T. Urata, and J. Mochizuki,
J. Antibiot., 1993, 46, 1859: M. Iwatsuki, E. Niki, and S. Kato, BioFactors, 1993, 4, 123. (b)
Carabazomadurins: N. Kotoda, K. Shin-ya, K. Furihata, Y. Hayakawa, and H. Seto, J.
Antibiot., 1997, 50. 770. (c) Antiostatins: C. J. Mo, K. Shin-ya, K. Furihata, K. Furihata, S.
Shimazu, Y. Hayakawa, and H. Seto, J. Antibiot., 1990, 43. 1337. (d) Neocarbazostatins: S.
Kato, K. Shindo, Y. Kataoka, Y. Yamagishi, and J. Mochizuki, J. Antibiot., 1991, 44. 903.
3. For recent reviews: (a) U. Pindur, Chimia, 1990, 44, 406. (b) J. Bergman and B. Pelcman,
Pure Appl. Chem., 1990, 62, 1967. (c) H.-J. Knölker, Synlett, 1992, 371. (d) T. Kawasaki
and M. Sakamoto, J. Indian Chem. Soc., 1994, 71. 443. (e) C. J. Moody, Synlett, 1994, 681.
(f) H.-J. Knölker, ‘Advances in Nitrogen Heterocycles’, Vol. 1, ed. by C. J. Moody, JAI Press:
Greenwich, CT(USA), 1995, p. 173. (g) S. Hibino and E. Sugino, ‘Advances in Nitrogen
Heterocycles’, Vol. 1, ed. by C. J. Moody, JAI Press: Greenwich, CT(USA), 1995, p. 205.
4. For the previous syntheses of carazostatin : (a) P. M. Jackson and C. J. Moody, Synlett, 1990,
521. P. M. Jackson, C. J. Moody, and R. J. Mortimer, J. Chem. Soc., Perkin Trans. 1, 1991
2941. (b) H. J. Knölker and T. Hopfman, Synlett, 1995, 981. (c) K. Shin and K. Ogasawara,
Chem. Lett., 1995, 289. (d) T. Choshi, T. Sada, H. Fujimoto, C. Nagayama, E. Sugino, and S.
Hibino, Tetrahedron Lett., 1996, 37, 2593: T. Choshi, T. Sada, H. Fujimoto, C. Nagayama, E.
Sugino, and S. Hibino, J. Org. Chem., 1997, 62, 2535.
5. (a) T. Kawasaki, Y. Nonaka, and M. Sakamoto, J. Chem. Soc., Chem. Commun., 1989, 43. (b)
T. Kawasaki, Y. Nonaka, M. Akahane, N. Maeda, and M. Sakamoto, J. Chem. Soc., Perkin
Trans. 1, 1993, 1777.
6. C. Chien, T. Suzuki, T. Kawasaki, and M. Sakamoto, Chem. Pharm. Bull., 1984, 32, 3945.
7. Carazostatin (1): mp 157.5-159 °C (from ether-hexane), (lit., mp 149-152 °C2a; 159-160 °C4d).
1H-NMR (400 MHz, CDCl3) δ: 0.89 (3H, t, J = 7 Hz), 1.20-1.50 (8H, m), 1.60-1.70 (2H, m),
2.37 (3H, s), 2.88 (2H, t, J = 8 Hz), 4.58 (1H, br s), 7.16 (1H, t, J = 8 Hz), 7.32-7.46 (3H, m),
7.75 (1H, br s), 7.93 (1H, d, J = 8 Hz). 13C-NMR (100 MHz, CDCl3) δ: 12.2, 14.4, 22.9, 29.1,
29.6, 29.8, 30.3, 32.2, 103.2, 110.9, 119.2, 120.3, 121.1, 121.6, 123.9, 124.4, 125.5, 134.2,
140.0, 148.4.