Synthesis of the C31–C67 Fragment of Amphidinol 3†
Javier de Vicente Dr.
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences 2, Irvine, CA 92697-2025, USA, Fax: (+1) 949-824-6379
Search for more papers by this authorJohn R. Huckins
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences 2, Irvine, CA 92697-2025, USA, Fax: (+1) 949-824-6379
Search for more papers by this authorScott D. Rychnovsky Prof.
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences 2, Irvine, CA 92697-2025, USA, Fax: (+1) 949-824-6379
Search for more papers by this authorJavier de Vicente Dr.
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences 2, Irvine, CA 92697-2025, USA, Fax: (+1) 949-824-6379
Search for more papers by this authorJohn R. Huckins
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences 2, Irvine, CA 92697-2025, USA, Fax: (+1) 949-824-6379
Search for more papers by this authorScott D. Rychnovsky Prof.
Department of Chemistry, University of California, Irvine, 1102 Natural Sciences 2, Irvine, CA 92697-2025, USA, Fax: (+1) 949-824-6379
Search for more papers by this authorThis study was supported by the National Institutes of General Medicine (GM 43854). J.d.V. acknowledges the Spanish Ministry of Education and Science for a postdoctoral fellowship.
Graphical Abstract
A tetrahydropyran intermediate, prepared from (−)-diethyl tartrate, was used to assemble the C31–C67 fragment of amphidinol 3. Both of the tetrahydropyran rings in the natural product were prepared from this intermediate. The polyene segment was assembled with high selectivity.
Supporting Information
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References
- 1
- 1aG. K. Paul, N. Matsumori, M. Murata, K. Tachibana, Tetrahedron Lett. 1995, 36, 6279;
- 1bM. Satake, M. Murata, T. Yasumoto, T. Fujita, H. Naoki, J. Am. Chem. Soc. 1991, 113, 9859;
- 1cT. Houdai, S. Matsuoka, M. Murata, M. Satake, S. Ota, Y. Oshima, L. L. Rhodes, Tetrahedron 2001, 57, 5551;
- 1dM. Murata, S. Matsuoka, N. Matsumori, G. K. Paul, K. Tachibana, J. Am. Chem. Soc. 1999, 121, 870;
- 1eG. K. Paul, N. Matsumori, K. Konoki, M. Murata, K. Tachibana, J. Mar. Biotech. 1997, 5, 124;
- 1fG. K. Paul, N. Matsumori, K. Konoki, M. Sasaki, M. Murata, K. Tachibana in Harmful and Toxic Algal Blooms. Proceedings of Seventh International Conference on Toxic Phytoplankton (Eds.: ), UNESCO, Sendai, Japan, 1996, p. 503.
- 2N. Matsumori, D. Kaneno, M. Murata, H. Nakamura, K. Tachibana, J. Org. Chem. 1999, 64, 866.
- 3
- 3aJ. de Vicente, B. Betzemeier, S. D. Rychnovsky, Org. Lett. 2005, 7, 1853;
- 3bS. BouzBouz, J. Cossy, Org. Lett. 2001, 3, 1451;
- 3cE. M. Flamme, W. R. Roush, Org. Lett. 2005, 7, 1411;
- 3dJ. D. Hicks, E. M. Flamme, W. R. Roush, Org. Lett. 2005, 7, 5509;
- 3eL. A. Paquette, S.-K. Chang, Org. Lett. 2005, 7, 3111;
- 3fS.-K. Chang, L. A. Paquette, Synlett 2005, 2915;
- 3gC. Dubost, I. E. Marko, J. Bryans, Tetrahedron Lett. 2005, 46, 4005.
- 4
- 4aL. Ayala, C. G. Lucero, J. A. C. Romero, S. A. Tobacco, K. A. Woerpel, J. Am. Chem. Soc. 2003, 125, 15521;
- 4bR. V. Stevens, A. W. M. Lee, J. Am. Chem. Soc. 1979, 101, 7032;
- 4cR. V. Stevens, Acc. Chem. Res. 1984, 17, 289;
- 4dP. Deslongchamps, Stereoelectronic Effects in Organic Chemistry, Pergamon, New York, 1983, pp. 209–221.
- 5J.-M. Brunel, P. Diter, M. Deutsch, H. B. Kagan, J. Org. Chem. 1995, 60, 8086.
- 6B. M. Trost, S. Mallart, Tetrahedron Lett. 1993, 34, 8025.
- 7The major isomer of 7 was purified by MPLC before the Mosher analysis:
- 7aM. J. Rieser, Y. H. Hui, J. K. Rupprecht, J. F. Kozlowski, K. V. Wood, J. L. McLaughlin, P. R. Hanson, Z. Zhuang, T. R. Hoye, J. Am. Chem. Soc. 1992, 114, 10203;
- 7bJ. A. Dale, H. S. Mosher, J. Am. Chem. Soc. 1973, 95, 512;
- 7cG. R. Sullivan, J. A. Dale, H. S. Mosher, J. Org. Chem. 1973, 38, 2143;
- 7dI. Ohtani, T. Kusumi, Y. Kashman, H. Kakisawa, J. Am. Chem. Soc. 1991, 113, 4092.
- 8
- 8aA. Basha, M. Lipton, S. M. Weinreb, Tetrahedron Lett. 1977, 18, 4171;
- 8bJ. I. Levin, E. Turos, S. M. Weinreb, Synth. Commun. 1982, 12, 989.
- 9D. L. Comins, A. Dehghani, Tetrahedron Lett. 1992, 33, 6299.
- 10W. J. Scott, J. K. Stille, J. Am. Chem. Soc. 1986, 108, 3033.
- 11R. Pappo, D. S. Allen, Jr.,R. U. Lemieux, W. S. Johnson, J. Org. Chem. 1956, 21, 478.
- 12D. B. Dess, J. C. Martin, J. Org. Chem. 1983, 48, 4155.
- 13
- 13aK. Sonagashira, Y. Todah, N. Hagihara, Tetrahedron Lett. 1975, 16, 4467;
- 13bM. Alami, F. Ferri, G. Linstrumelle, Tetrahedron Lett. 1993, 34, 6403.
- 14
- 14aH. C. Brown, S. K. Gupta, J. Am. Chem. Soc. 1972, 94, 4370;
- 14bH. C. Brown, T. Hamaoka, N. Ravindran, J. Am. Chem. Soc. 1973, 95, 5786.
- 15
- 15aE.-I. Negishi, Acc. Chem. Res. 1982, 15, 340;
- 15bE.-I. Negishi, T. Takahashi, S. Baba, D. E. Van Horn, N. Okukado, J. Am. Chem. Soc. 1987, 109, 2393.
- 16
- 16aS. L. Huang, K. Omura, D. Swern, J. Org. Chem. 1976, 41, 3329;
- 16bT. T. Tidwell, Org. React. 1990, 39, 297.
- 17Y. Wang, F. G. West, Synthesis 2002, 99.
- 18LiDBB is a reducing agent for arene radical anions, first reported by Freeman et al.: P. K. Freeman, L. L. Hutchinson, J. Org. Chem. 1980, 45, 1924.
- 19O. Mitsunobu, Synthesis 1981, 1.
- 20H. S. Schultz, H. B. Freyermuth, S. R. Buc, J. Org. Chem. 1963, 28, 1140.
- 21J. R. Parikh, W. v. E. Doering, J. Am. Chem. Soc. 1967, 89, 5505.
- 22
- 22aP. R. Blakemore, W. J. Cole, P. J. Kocienski, A. Morley, Synlett 1998, 26;
- 22bP. R. Blakemore, J. Chem. Soc. Perkin Trans. 1 2002, 2563.
- 23M. Julia, J. M. Paris, Tetrahedron Lett. 1973, 14, 4833.
