Total synthesis of NPTX-5 and NPTX-6, Joro spider (Nephila clavata) toxins having a unique putreanine trimer and putreanine tetramer acylpolyamine chain

Tetrahedron Letters

Volumn 39, Issue 36, 1998, Pages 6479-6482

  Saito, Hiroaki ^a   Yuri, Etsuko ^a   Miyazawa, Masahiro ^a   Itagaki, Yasuhiro ^b   Nakajima, Terumi ^b   Miyashita, Masaaki ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

^b SUNTORY INSTITUTE FOR BIOORGANIC RESEARCH   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

INDOLE DERIVATIVE; POLYAMINE; PUTREANINE; SPIDER VENOM; TETRAMER; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CHEMICAL STRUCTURE; FAST ATOM BOMBARDMENT MASS SPECTROMETRY; NEUROPHARMACOLOGY; NEUROTRANSMISSION; NONHUMAN; SPIDER; SYNTHESIS; TOXIN ANALYSIS;

ARANEAE; NEPHILA CLAVATA;

EID: 0032171333     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01379-3     Document Type: Article

References (27)

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2. 2 T. Toki, T. Yasuhara, Y. Aramaki, N. Kawai, and T. Nakajima, Biomedical Res., 1988, 9, 75; T. Toki, T. Yasuhara, Y. Aramaki, K. Osawa, A. Miwa, N. Kawai, and T. Nakajima, ibid., 1988, 9, 421.
3. 2 T. Toki, T. Yasuhara, Y. Aramaki, N. Kawai, and T. Nakajima, Biomedical Res., 1988, 9, 75; T. Toki, T. Yasuhara, Y. Aramaki, K. Osawa, A. Miwa, N. Kawai, and T. Nakajima, ibid., 1988, 9, 421.
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5. 4 M. Miyashita, H. Sato, M. Matsushita, Y. Kusumegi, T. Toki, A. Yoshikoshi, T. Yanami, Y. Kikuchi, C. Takasaki, T. Nakajima, and H. Irie, Tetrahedron Lett., 1992, 33, 2837.
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9. 8 M. Miyashita, J. Synth. Org. Chem. Japan, 1996, 54, 846.
10. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
11. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
12. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
13. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
14. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
15. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
16. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
17. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
18. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
19. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
20. 9 Synthesis of other spider toxins: NSTX-3: T. Teshima, T. Wakamiya, Y. Aramaki, T. Nakajima, N. Kawai, and T. Shiba, Tetrahedron Lett., 1987, 28, 3509; D. M. Nason, V. J. Jasys, P. R. Kelbaugh, D. Phillips, N. A. Saccomano, and R. A. Volkman, ibid., 1989, 30, 2337; T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, and T. Nakajima, Tetrahedron, 1990, 46, 3819; JSTX-3: Y. Hashimoto, Y. Endo, K. Shudo, Y. Aramaki, N. Kawai, and T. Nakajima, Tetrahedron Lett., 1987, 25, 3511; Argiotoxin: T. L. Shih, J. R-Sanchez, and H. Mrozik, ibid., 1987, 28, 6015; M. E. Adams, R. L. Carney, F. E. Enderlin, E. T. Fu, M. A. Jarema, J. P. Li, C. A. Miller, D. A. Schooley, M. J. Shapiro, and V. J. Venema, Biochem. Biophys. Res. Commun., 1987, 148, 678; V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, N. A. Saccomano, and R. A. Volkamann, Tetrahedron Lett., 1988, 29, 6223; Clavamine: T. Teshima, T. Matsumoto, M. Miyagawa, T. Wakamiya, T. Shiba, N. Narai, M. Yoshioka, T. Nakajima, and N. Kawai, ibid., 1990, 46, 3819; Agelenopsis aperta: V. J. Jasys, P. R. Kelbaugh, D. M. Nason, D. Phillips, K. J. Rosnack, N. A. Saccomano, J. G. Stroh, and R. A. Volkamann, J. Am. Chem. Soc., 1990, 112, 6696; NPTX-9 and 11: B. W. Bycroft, W. C. Chan, N. D. Hone, S. Millington, and I. A. Nash, J. Am. Chem. Soc., 1994, 116, 7415; FTX: I. S. Blagbrough and E. Moya, Tetrahedron Lett., 1994, 35, 2057.
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24. 12 D. Batcho and W. Leimgruber, Org, Synth., 1985, 63, 214; A. Stoll, F. Troxler, J. Peyer, and A. Hofmann, Helv. Chim. Acta 1955, 38, 1452.
25. 13 Deprotection of the left-half segment 13 using TFA was unsuccessful.
26. 14 Y. Itagaki, T. Fujita, H. Naoki, T. Yasuhara, M. Andriantsiferana, and T. Nakajima, Natural Toxins, 1997, 5, 1.
27. 1H-NMR (270 MHz) spectra of the synthetic compounds were also in agreement with the proposed structures, although those of the natural toxins have not been measured yet owing to its limited quantity.