Total synthesis of sulfur-containing pyrroloiminoquinone marine product, (±)-makaluvamine F using hypervalent iodine(III)-induced reactions

Abstract

The first total synthesis of potent cytotoxic makaluvamine F 1, a sulfur-containing pyrroloiminoquinone marine product, has been accomplished using hypervalent iodine(III)-induced reactions.

References

1. D. C. Radisky, E. S. Radisky, L. R. Barrows, B. R. Copp, R. A. Kramer and C. M. Ireland, J. Am. Chem. Soc., 1993, 115, 1632.
2. L. R. Barrows, D. C. Radisky, B. R. Copp, D. S. Swaffar, R. A. Kramer, R. L. Warters and C. M. Ireland, Anti-Cancer Drug Des., 1993, 8, 333.
3. J.-F. Cheng, Y. Ohizumi, M. R. Wälchli, H. Nakamura, Y. Hirata, T. Sasaki and J. Kobayashi, J. Org. Chem., 1988, 53, 4621; H. H. Sun, S. Sakemi, N. Burres and P. McCarthy, J. Org. Chem., 1990, 55, 4964; J. W. Blunt, M. H. G. Munro, C. N. Battershill, B. R. Copp, J. D. McCombs, N. B. Perry, M. R. Prinsep and A. M. Thompson, New Chem., 1990, 14, 761; J. Kobayashi, J.-F. Cheng, S. Yamamura and M. Ishibashi, Tetrahedron Lett., 1991, 32, 1227 and references cited therein; T. F. Molinski, Chem. Rev., 1993, 93, 1825; B. R. Copp, K. F. Fulton, N. B. Perry, J. W. Blunt and M. H. G. Munro, J. Org. Chem., 1994, 59, 8233; A. Yang, B. J. Baker, J. Grimwade, A. Leonard and J. B. McClintock, J. Nat. Prod., 1995, 58, 1596.
4. Y. Kita, T. Yakura, H. Tohma, K. Kikuchi and Y. Tamura, Tetrahedron Lett., 1989, 30, 1119; H. J. Knölker and K. Hartmann, Synlett, 1991, 428; S. Hamabuchi, H. Hamada and M. Somei, Heterocycles, 1991, 32, 443; S. Nishiyama, J.-F. Cheng, X. L. Tao and S. Yamamura, Tetrahedron Lett., 1991, 32, 4151; T. Izawa, S. Nishiyama and S. Yamamura, Tetrahedron, 1994, 50, 13593; J. D. White, K. M. Yager and T. Yakura, J. Am. Chem. Soc., 1994, 116, 1831; E. V. Sadanandan, S. K. Pillai, M. V. Lakshmikantham, A. D. Billimoria, J. S. Culpepper and M. P. Cava, J. Org. Chem., 1995, 60, 1800; D. Roberts, M. Alvarez and J. A. Joule, Tetrahedron Lett., 1996, 37, 1509; R. Zhao and J. W. Lown, Synth. Commun., 1997, 27, 2103; D. Roberts, J. A. Joule, M. A. Bros and M. Alvarez, J. Org. Chem., 1997, 62, 568; M. Makosza, J. Stalewski and O. S. Maslennikova, Synthesis, 1997, 1131; M. Iwao, O. Motoi, T. Fukuda and F. Ishibashi, Tetrahedron, 1998, 54, 8999; G. A. Kraus and N. Selvakumar, Synlett, 1998, 845.
5. Y. Kita, H. Tohma, M. Inagaki, K. Hatanaka and T. Yakura, J. Am. Chem. Soc., 1992, 114, 2175.
6. Y. Kita, M. Egi, A. Okajima, M. Ohtsubo, T. Takada and H. Tohma, Chem. Commun., 1996, 1491; Y. Kita, H. Watanabe, M. Egi, T. Saiki, Y. Fukuoka and H. Tohma, J. Chem. Soc., Perkin Trans. 1, 1998, 635.
7. Y. Kita, M. Egi, M. Ohtsubo, T. Saiki, T. Takada and H. Tohma, Chem. Commun., 1996, 2225.
8. H. Böhme and D. Morf, Chem. Ber., 1957, 90, 446.
9. H. Böhme and F. Ziegler, Liebigs Ann. Chem., 1974, 734; I. W. J. Still, W. L. Brown, R. J. Colville and G. W. Kutney, Can. J. Chem., 1984, 62, 586.
10. B. M. Trost, M. Vaultier and M. L. Santiago, J. Am. Chem. Soc., 1980, 102, 7929.
11. H. Tohma, M. Egi, M. Ohtsubo, H. Watanabe, S. Takizawa and Y. Kita, Chem. Commun., 1998, 173.