An approach to the synthesis of the eupomatilones

Organic Letters

Volumn 4, Issue 1, 2002, Pages 19-20

  Hong, Sang Phyo ^a   McIntosh, Matthias C ^a  

^a UNIVERSITY OF ARKANSAS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LIGNAN;

ARTICLE; AUSTRALIA; CHEMISTRY; CONFORMATION; MAGNOLIACEAE; PLANT; STEREOISOMERISM; SYNTHESIS;

AUSTRALIA; INDICATORS AND REAGENTS; LIGNANS; MAGNOLIACEAE; MOLECULAR CONFORMATION; PLANTS; STEREOISOMERISM;

EID: 0037050433     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0167816     Document Type: Article

References (32)

1. Carroll, A. R.; Taylor, W. C. Aust. J. Chem. 1991, 44, 1705-1714.
2. For a recent review of lignans, see: Ward, R. S. Nat. Prod. Rep. 1997, 14, 43-74.
3. Both atropisomers occur naturally and were not chromatographically separable (ref 1).
4. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877. Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650-657. Ireland, R. E.; Wipf, P.; Xiang, J.-N. J. Org. Chem. 1991, 56, 3572-3582.
5. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877. Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650-657. Ireland, R. E.; Wipf, P.; Xiang, J.-N. J. Org. Chem. 1991, 56, 3572-3582.
6. Ireland, R. E.; Mueller, R. H.; Willard, A. K. J. Am. Chem. Soc. 1976, 98, 2868-2877. Ireland, R. E.; Wipf, P.; Armstrong, J. D. J. Org. Chem. 1991, 56, 650-657. Ireland, R. E.; Wipf, P.; Xiang, J.-N. J. Org. Chem. 1991, 56, 3572-3582.
7. For reviews, see: Wipf, P. In Comprehensive Organic Synthesis; Trost. B. M., Ed.; Pergamon: New York, 1991; Vol. 5, pp 827-873. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Frauenrath, H. In Stereoselective Synthesis, 4th ed.; Heichen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3301-3756.
8. For reviews, see: Wipf, P. In Comprehensive Organic Synthesis; Trost. B. M., Ed.; Pergamon: New York, 1991; Vol. 5, pp 827-873. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Frauenrath, H. In Stereoselective Synthesis, 4th ed.; Heichen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3301-3756.
9. For reviews, see: Wipf, P. In Comprehensive Organic Synthesis; Trost. B. M., Ed.; Pergamon: New York, 1991; Vol. 5, pp 827-873. Pereira, S.; Srebnik, M. Aldrichimica Acta 1993, 26, 17-29. Frauenrath, H. In Stereoselective Synthesis, 4th ed.; Heichen, G., Hoffmann, R. W., Mulzer, J., Schaumann, E., Eds.; Georg Thieme Verlag: Stuttgart, 1995; Vol. E21d, pp 3301-3756.
10. Zhang, X.; McIntosh, M. C. Tetrahedron Lett. 1998, 39, 7043-7046. McIntosh, M. C.; Hong, S.-p.; Lindsay, H. A.; Yaramasu, T.; Zhang, X. Submitted for publication.
11. Zhang, X.; McIntosh, M. C. Tetrahedron Lett. 1998, 39, 7043-7046. McIntosh, M. C.; Hong, S.-P.; Lindsay, H. A.; Yaramasu, T.; Zhang, X. Submitted for publication.
12. Hong, S.-P.; McIntosh, M. C. Tetrahedron 2001, 57, 5055-5060.
13. 2, tBuOOH, mCPBA, MMPP, and NaOCl. Over-oxidation was likely the principal side reaction: McKillop, A.; Taylor, R. J. K.; Watson, R. J.; Lewis, N. J. Chem. Soc., Chem. Commun. 1992, 1589-1591.
14. Smith, A. B., III; Brancca, S. J.; Pilla, N. N.; Gaciaro, M. A. J. Org. Chem. 1982, 47, 1855-1869.
15. Tsui, H.-C.; Paquette, L. A. J. Org. Chem. 1998, 63, 9968-9977.
16. The anti addition is based on ample precedent: Taylor, R. J. K.; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775-790. Wipf, P.; Coish, P. D. G. J. Org. Chem. 1999, 64, 5053-5061 and references therein.
17. The anti addition is based on ample precedent: Taylor, R. J. K.; Alcaraz, L.; Kapfer-Eyer, I.; Macdonald, G.; Wei, X.; Lewis, N. Synthesis 1998, 775-790. Wipf, P.; Coish, P. D. G. J. Org. Chem. 1999, 64, 5053-5061 and references therein.
18. 3 carbon of epoxy acid 8 appears at 19.3 ppm. (c) The (E)-alkene geometry was confirmed by NOESY.
19. Eshelby, J. J.; Parsons, P. J.; Sillars, N. C.; Crowley, P. J. J. Chem. Soc., Chem. Commun. 1995, 1497-1498.
20. N2′pathway: Chouteau, F.; Addi, K.; Bénéchie, M.; Prangé, T.; Huuong-Huu, F. Tetrahedron 2001, 57, 6229-6238.
21. (a) For reviews of allylic strain directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370. Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860.
22. (a) For reviews of allylic strain directed reactions, see: Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307-1370. Hoffman, R. W. Chem. Rev. 1989, 89, 1841-1860.
23. N2′ reaction, see: Magid, R. M. Tetrahedron 1980, 36, 1901-1930. Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423.
24. N2′ reaction, see: Magid, R. M. Tetrahedron 1980, 36, 1901-1930. Paquette, L. A.; Stirling, C. J. M. Tetrahedron 1992, 48, 7383-7423.
25. 5 proton might arise from nOe interactions with either or both methyl groups.
26. Churcher, I.; Hallett, D.; Magnus, P. J. Am. Chem. Soc. 1998, 120, 10350-10358.
27. Suginome, H.; Onto, K.; Yorita, K.; Ishikawa, M.; Shimoyama, N.; Sasaki, T. J. Org. Chem. 1995, 60, 3052-3064.
28. For a review, see: Farina, V.; Krishnamurthy, V.; Scott, W. J. Org. React. 1996, 50, 1-652.
29. (a) Ley, S. V.; Cox, L. R.; Meek, G.; Metten, K.-H.; Pique, C.; Worrall, J. M. J. Chem. Soc., Perkin Trans. 1 1997, 3299-3313.
30. 3COOK resulted in epoxidation only of the proximal alkene; cf. Corey, E. J.; Wu, L. I. J. Am. Chem. Soc. 1993, 115, 9327-9328.
31. 13C NMR spectra.
32. Pak, C. S.; Lee, E.; Lee, G. H. J. Org. Chem. 1993, 58, 1523-1530.