Enantiospecific synthesis of N-Boc-Adda: A linear approach

Organic Letters

Volumn 2, Issue 18, 2000, Pages 2901-2903

  Pearson, Clay ^a   Rinehart, Kenneth L ^a   Sugano, Michihiro ^a   Costerison, Jennifer R ^a  

^a UNIVERSITY OF ILLINOIS AT URBANA CHAMPAIGN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINO ACID; BACTERIAL TOXIN; DECANOIC ACID DERIVATIVE; FORMIC ACID DERIVATIVE; T BUTYLOXYCARBONYL GROUP; T-BUTYLOXYCARBONYL GROUP;

ARTICLE; CHEMISTRY; CYANOBACTERIUM; STEREOISOMERISM; SYNTHESIS;

AMINO ACIDS; BACTERIAL TOXINS; CYANOBACTERIA; DECANOIC ACIDS; FORMIC ACID ESTERS; STEREOISOMERISM;

EID: 0034618309     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol006347o     Document Type: Article

References (20)

1. 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, 8557-8558.
2. Silva, D.; Williams, D. E.; Andersen, R. J.; Klix, H.; Holmes, C. F. B.; Allen, T. M. Tetrahedron Lett. 1992, 33, 1561-1564.
3. Rinehart, K. L.; Namikoshi, M.; Choi, B. W. J. Appl. Phycol. 1994, 6, 159-176.
4. Mehrotra, A. P.; Gani, D. Tetrahedron Lett. 1996, 37, 6915-6918 and references therein.
5. (a) Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349-4352.
6. (b) Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1990, 30, 2043-2046.
7. (c) Beatty, M. F.; Jennings-White, C.; Avery, M. A. J. Chem. Soc., Perkin Trans. 1 1992, 1637-1641.
8. (d) Schreiber, S. L.; Valentekovich, R. J. J. Am. Chem. Soc. 1995, 117, 9069-9070.
9. (e) Humphrey, J. M.; Aggen, J. B.; Chamberlin A. R. J. Am. Chem. Soc. 1996, 118, 11759-11770.
10. (f) Sin, N.; Kallmerten, J. Tetrahedron Lett. 1996, 37, 5645-5648.
11. (g) D'Aniello, F.; Mann, A. J. Org. Chem. 1996, 61, 4870-4871.
12. (h) Kim, H. Y.; Toogood, P. L. Tetrahedron Lett. 1996, 37, 2349-2352.
13. (i) Panek, J. S.; Hu, T. J. Org. Chem. 1997, 62, 4914-4915.
14. (j) Cundy, D. L.; Donohue, A. C.; McCarthy, T. D. J. Chem. Soc., Perkin Trans. 1 1999, 559-567.
15. Evans, D. A. Aldrichimica Acta. 1982, 15, 23-32.
16. Baldwin, J. E.; Adlington, R. M.; Mellor, L. C. Tetrahedron 1994, 50, 5049-5066.
17. 3 gave good yields of the azide but with complete loss of stereocontrol (possibly due to [3,3] sigmatropic rearrangement). Mitsunobu reactions were also tested with phthalimide and N-(tert-butoxycarbonyl)-p-toluenesulfonamide, but the yields were low and stereocontrol was poor.
18. (a) Keck, G. E.; McHardy, S. F.; Wager, T. T. Tetrahedron Lett. 1995, 36, 7419-7422.
19. (b) Guagnano, V. M.S. Thesis, University of Illinois at Urbana-Champaign, January 1997.
20. Pearson, J. C.; Rinehart, K. L.; Sugano, M. Tetrahedron Lett. 1999, 40, 411-414.