Convergent synthesis of (+)-muconin

Tetrahedron Letters

Volumn 40, Issue 44, 1999, Pages 7827-7830

  Yang, Wen Qian ^a   Kitahara, Takeshi ^a  

^a UNIVERSITY OF TOKYO   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACETOGENIN; DEXTRO GLUTAMIC ACID; MUCONIN; PALLADIUM; TETRAHYDROPYRAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL MODIFICATION; DRUG SYNTHESIS; STEREOCHEMISTRY;

EID: 0033615769     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)01629-9     Document Type: Article

References (23)

1. 1. a) Cavé, A.; Figadère, B.; Laurens, A.; Cortes, D. Progress in the Chemistry of Natural Products 1997, 70, 81.
2. b) Zeng, L.; Ye, Q.; Oberlies, N. H.; Shi, G.; Gu, Z.-M.; He, K.; McLaughlin, J. L. Natural Product Reports 1996, 13, 275.
3. 2. Shi, G.; Kozlowski, J. F.; Schwedler, J. T.; Wood, K.V.; MacDougal, J. M; McLaughlin, J. L. J. Org. Chem. 1996, 61, 7988.
4. 3. For the first total synthesis of 1, see: Schaus, S. E.; Brånalt, J.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 4876.
5. 4. Koert, U.; Stein, M.; Wagner, H. Liebigs Ann. 1995, 1415.
6. 5. Kuriyama, W.; Ishigami, K.; Kitahara, T. Heterocycles 1999, 50, 981.
7. 6. Bromide 4 was prepared as follows. (formula presented)
8. 7. Grignard reaction of 3 under various conditions is shown below. (formula presented) (table presented)
9. 8b
10. b) Born, L.; Lieb, F. J.; Lorentzen, P.; Moeschler, H.; Nonfon, M.; Söllner, R.; Wendisch, D. Planta Med. 1990, 56, 312.
11. 9. The cis-THP ring of 7 was confirmed by the positive NOESY correlation at H-13/17.
12. 10. a) Dess, D. B.; Martin, J. C. J. Org. Chem. 1983, 48, 4155.
13. b) Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
14. c) Ireland, R. E.; Liu, L. J. Org. Chem. 1993, 58, 2899.
15. 11. Fernandez-Megia, E.; Gourlaouen, N.; Ley, S. V; Rowlands, G. J. Synlett 1998, 991.
16. 12. The stereochemistry of two isomers in 9 was assigned by converting them to the corresponding muconin and C12-epi-muconin.
17. 13. Larcheveque, M.; Lalande, J. Tetrahedron 1984, 40,1061.
18. 14. a) Mori, K. Tetrahedron 1975, 31, 3011.
19. b) Ishigami, K.; Kitahara, T. Tetrahedron 1995, 51, 6431.
20. 14b
21. 16. Nicolaou, K. C.; Liu, A.; Zeng, Z.; McComb, S. J. Am. Chem. Soc. 1992, 114, 9279.
22. 17. Elbaum, D.; Nguyen, T. B.; Jorgensen, W. L.; Schreiber, S. L. Tetrahedron 1994, 50, 1503.
23. 3) δ 0.87 (3H, t, J= 7.0 Hz), 1.20-2.20 (49H, m), 1.43 (3H, d, J = 6.5 Hz), 2.37 (1H, m), 2.52 (1H, m), 3.16 (1H, m), 3.31 (1H, m), 3.38 (1H, m), 3.43 (1H, m), 3.77-3.90 (3H, m), 5.06 (1H, m), 7.18 (1H, d, J=0.5 Hz).