A new stereoselective route to (2S, 3S, 8S, 9S, 4E, 6E)-3-amino-9-methoxy-2, 6, 8-trimethyl-10-phenyldeca-4, 6-dienoic acid (Adda)

Tetrahedron Letters

Volumn 37, Issue 14, 1996, Pages 2349-2352

  Kim, Hong Yong ^a   Toogood, Peter L ^a  

^a UNIVERSITY OF MICHIGAN   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

3 AMINO 9 METHOXY 2,6,8 TRIMETHYL 10 PHENYLDECA 4,6 DUNOIC ACID; AMINO ACID DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHIRALITY; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0029997256     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)00282-1     Document Type: Article

References (21)

1. 2O, di-tert-butyl dicarbonate; DBU, 1,8-diazabicyclo[5.4.0]undec-7-ene; DEAD, diethylazodicarboxylate; DMS, dimethyl sulfide, DMSO, dimemylsulfoxide; DPPA, diphenylpbosphoryl azide; KHMDS, potassium bis(trimethylsilyl) amide; LDA, lithium diisopropylamide; THF, tetrahydrofuran; TMSCl, trimethylsilyl chloride.
2. (a) Carmichael, W. W.; Beasley, V. R.; Brunner, D. L.; Eloff, J. N.; Falconer, I.; Gorham, P.; Harada, K.-I.; Krishnamurthy, T.; Yu, M.-J.; Moore, R. E.; Rinehart, K. L.; Runnegar, M.; Skulberg, O. M.; Watanabe, M. F. Toxicon 1988, 26, 971-973.
3. (b) Namikoshi, M.; Sun, F.; Choi, B. W.; Rinehart, K. L.; Carmichael, W. W. Evans, W. R.; Beasley, V. R. J. Org. Chem. 1995, 60, 3671-3679 and references therein.
4. Rinehart, K. L.; Harada, K.; Namikoshi, M.; 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.
5. Dilip de Silva, E.; Williams, D. E.; Anderson, R. J.; Klix, H.; Holmes, C. F. B.; Allen, T. M. Tetrahedron Lett. 1992, 33, 1561-1564.
6. Namikoshi, M.; Rinehart, K. L.; Dahlem, A. M.; Beasley, V. R.; Carmichael, W. W. Tetrahedron Lett. 1989, 30, 4349-4352.
7. Beatty, M. F.; White, C. J.; Avery, M. A. J. Chem. Soc., Perkin. Trans. 1. 1992, 1637-1641.
8. Chakraborty, T. K.; Joshi, S. P. Tetrahedron Lett. 1990, 31, 2043-2046.
9. Schreiber, S. L.; Valentekovich, R. J. J. Am. Chem. Soc. 1995, 117, 9069-9070.
10. Koosha, K.; Berlan, J.; Capmau, M. L.; Chodkiewiez W. Bull. Soc. Chim. Fr. 1975, 1291-1294.
11. (a) Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2876.
12. (b) Ireland, R. E.; Varney, M. D. J. Am. Chem. Soc. 1984, 106, 3668-3670.
13. (c) Gould, T. J.; Balestra, M.; Wittman, M. D.; Gary, J. A.; Rossano, L. T.; Kallmerten, J. J. Org. Chem. 1987, 52, 3889-3901.
14. Fujisawa, T.; Tajima, K.; Sato, T. Chem. Lett. 1984, 1669-1672.
15. A derivative of compound 8, prepared by ozonolysis followed by reduction to the alcohol, then acylation with (1S)-(-)-camphanic chloride, indicates that 8 is formed with >95% enantioselectivity.
16. Thompson, A. S.; Humphrey, G. R.; DeMarco, A. M.; Mathre, D. J.; Grabowski, E. J. J. J. Org. Chem. 1993, 58, 5886-5888.
17. Examination of the mandelate ester prepared from compound 16 by saponification followed by condensation with methyl (S)-(+) mandelate indicates that 16 is formed with >95% enantioselectivity.
18. Kazmaier, U. Angew. Chem . Int. Ed. Engl. 1994, 33, 998-999.
19. Marshall, J. A.; Garafalo, A. W. J. Org. Chem. 1993, 55, 3675-3680.
20. The diastereomers of aldehyde 3 are separable by flash column chromatography.
21. + calcd. 446.2906, found 446.2884.