Total synthesis of pumiliotoxins A and 225F [2]

Journal of the American Chemical Society

Volumn 121, Issue 42, 1999, Pages 9873-9874

  Hirashima, Shintaro ^a   Aoyagi, Sakae ^a   Kibayashi, Chihiro ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; PUMILIOTOXIN;

CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; CHEMICAL STRUCTURE; LETTER; MASS SPECTROMETRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0033610482     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja991918x     Document Type: Letter

References (35)

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4. The pumiliotoxin subclass of alkaloids belongs to the pumiliotoxin A class of "dendrobatid alkaloids" together with the closely related subclasses of allopumiliotoxins and homopumiliotoxins.
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30. For examples of other applications of organozinc couplings in natural products synthesis, see: (a) Tius, M. A.; Gomez-Galeno, J.; Gu, X.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775. (b) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558. (c) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (d) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158. (e) Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W.; Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Bertounesque, E.; Salvatore, B. A. J. Org. Chem. 1998, 63, 7596. (f) Hu, T.; Panek, J. S. J. Org. Chem. 1999, 64, 3000.
31. For examples of other applications of organozinc couplings in natural products synthesis, see: (a) Tius, M. A.; Gomez-Galeno, J.; Gu, X.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775. (b) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558. (c) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (d) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158. (e) Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W.; Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Bertounesque, E.; Salvatore, B. A. J. Org. Chem. 1998, 63, 7596. (f) Hu, T.; Panek, J. S. J. Org. Chem. 1999, 64, 3000.
32. For examples of other applications of organozinc couplings in natural products synthesis, see: (a) Tius, M. A.; Gomez-Galeno, J.; Gu, X.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775. (b) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558. (c) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (d) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158. (e) Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W.; Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Bertounesque, E.; Salvatore, B. A. J. Org. Chem. 1998, 63, 7596. (f) Hu, T.; Panek, J. S. J. Org. Chem. 1999, 64, 3000.
33. For examples of other applications of organozinc couplings in natural products synthesis, see: (a) Tius, M. A.; Gomez-Galeno, J.; Gu, X.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775. (b) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558. (c) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (d) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158. (e) Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W.; Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Bertounesque, E.; Salvatore, B. A. J. Org. Chem. 1998, 63, 7596. (f) Hu, T.; Panek, J. S. J. Org. Chem. 1999, 64, 3000.
34. For examples of other applications of organozinc couplings in natural products synthesis, see: (a) Tius, M. A.; Gomez-Galeno, J.; Gu, X.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775. (b) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558. (c) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (d) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158. (e) Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W.; Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Bertounesque, E.; Salvatore, B. A. J. Org. Chem. 1998, 63, 7596. (f) Hu, T.; Panek, J. S. J. Org. Chem. 1999, 64, 3000.
35. For examples of other applications of organozinc couplings in natural products synthesis, see: (a) Tius, M. A.; Gomez-Galeno, J.; Gu, X.; Zaidi, J. H. J. Am. Chem. Soc. 1991, 113, 5775. (b) Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558. (c) Smith, A. B., III; Qiu, Y.; Jones, D. R.; Kobayashi, K. J. Am. Chem. Soc. 1995, 117, 12011. (d) Amat, M.; Hadida, S.; Pshenichnyi, G.; Bosch, J. J. Org. Chem. 1997, 62, 3158. (e) Smith, A. B., III; Friestad, G. K.; Duan, J. J.-W.; Barbosa, J.; Hull, K. G.; Iwashima, M.; Qiu, Y.; Spoors, P. G.; Bertounesque, E.; Salvatore, B. A. J. Org. Chem. 1998, 63, 7596. (f) Hu, T.; Panek, J. S. J. Org. Chem. 1999, 64, 3000.