Convergent synthesis of (2R,3R,8R,9R)-N-Boc-ADDA

Journal of Organic Chemistry

Volumn 73, Issue 13, 2008, Pages 5015-5021

  Meiries, Sebastien ^a   Marquez, Rodolfo ^a  

^a UNIVERSITY OF GLASGOW   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

AMERICAN CHEMICAL SOCIETY (ACS); CONVERGENT SYNTHESIS; CROSS METATHESIS (CM); ENANTIO; HIGHLY EFFICIENT; METHOXY;

AMINES;

3 AMINO 9 METHOXY 2,6,8 TRIMETHYL 10 PHENYLDECADIENOIC ACID; ALKADIENE; ALKENE; BETA AMINO ACID; MICROCYSTIN; MOTUPORIN; NODULARIN; PHOSPHOPROTEIN PHOSPHATASE INHIBITOR;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL STRUCTURE; CYANOBACTERIUM; DIASTEREOISOMER; ENANTIOMER; ENZYME INHIBITION; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; MARINE ENVIRONMENT; METHODOLOGY; NONHUMAN; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE (PORIFERA); SYNTHESIS; THEONELLA;

ALKENES; DECANOIC ACIDS; MODELS, MOLECULAR; MOLECULAR STRUCTURE; PHOSPHOPROTEIN PHOSPHATASES;

EID: 46849095656     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800574g     Document Type: Article

References (35)

1. Launey, T.; Endo, S.; Sakai, R.; Harano, J.; Ito, M. Proc. Nat. Acad. U.S.A. 2004, 101, 676.
2. (a) McCluskey, A.; Sakoff, J. A. Mini Rev. Med. Chem. 2001, 1, 43.
3. (b) McCluskey, A.; Sim, A. T. R.; Sakoff, J. A. J. Med. Chem. 2002, 45, 1151.
4. (a) Rinehart, K. L.; Harada, K.; Namikoshi, M.; Chen, C.; Harvis, C. A.; Munro, M. H. G.; Blunt, J. W.; Mulligan, P. E.; Beasley, V. R.; Dahlem, A. M.; Carmichael, W. W. J. Am. Chem. Soc. 1988, 110, 8557.
5. (b) Dilip de Silva, E.; Williams, D. E.; Andersen, R. J.; Klix, H.; Holmes, C. F. B.; Allen, T. M. Tetrahedron Lett. 1992, 33, 1561.
6. (a) Aggen, J. B.; Humphrey, J. M.; Gauss, C. M.; Huang, H. B.; Nairn, A. C.; Chamberlin, A. R. Bioorg. Med. Chem. 1999, 7, 543.
7. (b) Sheppeck, J. E., II; Gauss, C. M.; Chamberlin, A. R. Bioorg. Med. Chem. 1997, 5, 1739.
8. Blom, J. F.; Juttner, F. Toxicon 2005, 46, 465.
9. (a) Cundy, D. J.; Donohue, A. C.; McCarthy, T. D. J. Chem. Soc., Perkin Trans. 1 1999, 559.
10. (b) Panek, J. S.; Hu, T. J. Org. Chem. 1997, 62, 4914.
11. (c) Kim, H. Y.; Toogood, P. L. Tetrahedron Leu. 1996, 37, 2349.
12. (d) D'Aniello, F.; Mann, A.; Taddei, M. J. Org. Chem. 1996, 61, 4870.
13. (e) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1996, 37, 5645.
14. (f) Humphrey, J. M.; Aggen, J. B.; Chamberlin, A. R. J. Am. Chem. Soc. 1996, 118, 11759.
15. (g) Valentekovich, R. J.; Schreiber, S. L. J. Am. Chem. Soc. 1995, 117, 9069.
16. (h) Beatty, M. F.; Jennings-White, C.; Avery, M. A. J. Chem. Soc., Perkin Trans. 1 1992, 1637.
17. (i) Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1990, 31, 2043.
18. (j) Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349.
19. (k) Pearson, C.; Rinehart, K. L.; Sugano, M.; Costerison, J. R. Org. Lett. 2000, 2, 2901.
20. (l) Hu, T.; Panek, J. S. J. Org. Chem. 1999, 64, 3000.
21. (m) Bauer, S. M.; Armstrong, R. W. J. Am. Chem. Soc. 1999, 121, 6355.
22. Gulledge, B. M.; Aggen, J. B.; Eng, H.; Sweimeh, K.; Chamberlin, A. R. Bioorg. Med. Chem. Lett. 2003, 13, 2907.
23. Gulledge, B. M.; Aggen, J. B.; Huang, H. B.; Nairn, A. C.; Chamberlin, A. R Curr. Med. Chem. 2002, 9, 1991.
24. Rinehart, K. L.; Namikoshi, M.; Choi, B. Y. J. App. Phycol. 1994, 6, 159.
25. Wegerski, C. J.; Hammond, J.; Tenney, K.; Matainaho, T.; Crews, P. J. Nat. Prod. 2007, 70, 89.
26. (a) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1993, 115, 12208.
27. (b) Jung, M. E.; D'Amico, D. C. J. Am. Chem. Soc. 1997, 119, 12150.
28. (c) Jung, M. E.; Lee, W. S.; Sun, D. Org. Lett. 1999, 1, 307.
29. (d) Jung, M. E.; Marquez, R. Org. Lett. 2000, 2, 1669.
30. Kondo, H.; Oritani, T.; Kiyota, H. Eur. J. Org. Chem. 2000, 3459.
31. Firestone, R. A.; Barker, P. L.; Pisano, J. M.; Ashe, B. M.; Dahlgren, M. E. Tetrahedron 1990, 46, 2255.
32. Cheung, K. M.; Shoolingin-Jordan, P. M. Tetrahedron 1997, 53, 15807.
33. Chatterjee, A. K.; Choi, T. L.; Sanders, D. P.; Grubbs, R. H. J. Am. Chem. Soc. 2003, 125, 11360.
34. (a) Dewi, P.; Randl, S.; Blechert, S. Tetrahedron Lett. 2005, 46, 577.
35. (b) Moura-Letts, G.; Curran, D. P. Org. Lett. 2007, 9, 5.