Total synthesis of (-)-motuporin

Journal of Organic Chemistry

Volumn 64, Issue 9, 1999, Pages 3000-3001

  Hu, Tao ^a   Panek, James S ^a  

^a BOSTON UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKADIENE; CYCLOPEPTIDE; PALLADIUM; PENTAPEPTIDE;

ARTICLE; CATALYSIS; CROSS REACTION; CYCLIZATION; METHODOLOGY; PEPTIDE SYNTHESIS; STEREOCHEMISTRY;

EID: 0033617397     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9904617     Document Type: Article

References (31)

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7. Synthesis of Adda derivatives: (a) Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349-4352. (b) Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1990, 31, 2043-2046. Beatty, M. F.; White, C. J.; Avery, M. A. J. Chem. Soc., Perkin Trans. 1 1992, 1637-1641. Kim, H. Y.; Toogood, P. L. Tetrahedron Lett. 1996, 37, 2349-2352. (e) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871. (f) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1998, 37, 5645-5648. (g) Cundy, D. J.; Donohue, A. C.; McCarthy, T. D. Tetrahedron Lett. 1998, 39, 5125-5128.
8. Synthesis of Adda derivatives: (a) Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349-4352. (b) Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1990, 31, 2043-2046. Beatty, M. F.; White, C. J.; Avery, M. A. J. Chem. Soc., Perkin Trans. 1 1992, 1637-1641. Kim, H. Y.; Toogood, P. L. Tetrahedron Lett. 1996, 37, 2349-2352. (e) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871. (f) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1998, 37, 5645-5648. (g) Cundy, D. J.; Donohue, A. C.; McCarthy, T. D. Tetrahedron Lett. 1998, 39, 5125-5128.
9. Synthesis of Adda derivatives: (a) Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349-4352. (b) Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1990, 31, 2043-2046. Beatty, M. F.; White, C. J.; Avery, M. A. J. Chem. Soc., Perkin Trans. 1 1992, 1637-1641. Kim, H. Y.; Toogood, P. L. Tetrahedron Lett. 1996, 37, 2349-2352. (e) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871. (f) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1998, 37, 5645-5648. (g) Cundy, D. J.; Donohue, A. C.; McCarthy, T. D. Tetrahedron Lett. 1998, 39, 5125-5128.
10. Synthesis of Adda derivatives: (a) Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349-4352. (b) Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1990, 31, 2043-2046. Beatty, M. F.; White, C. J.; Avery, M. A. J. Chem. Soc., Perkin Trans. 1 1992, 1637-1641. Kim, H. Y.; Toogood, P. L. Tetrahedron Lett. 1996, 37, 2349-2352. (e) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870-4871. (f) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1998, 37, 5645-5648. (g) Cundy, D. J.; Donohue, A. C.; McCarthy, T. D. Tetrahedron Lett. 1998, 39, 5125-5128.
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21. More conventional cross-coupling protocols such as the Stille coupling reaction proved to be less efficient, as only modest yield (20-50%) was achieved. In addition, considerable levels of double bond isomerization occurred during the cross-coupling reactions.
22. To our knowledge, this is the first documentation of a Negishi-type coupling reaction performed with a peptide system. It is notable that this strategy may be suitable for the preparation of structurally diverse cyclicpeptides for the SAR study of the motuporin family.
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24. For preparation of this compound, see Supporting Information.
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29. 1H NMR (400 MHz).
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