Diastereoselective [4+2] reactions of o-quinone methides with a chiral enol ether: Asymmetric synthesis of (+)-R-mimosifoliol

Synlett

Volumn , Issue 6, 2004, Pages 1101-1103

  Selenski, Carolyn ^a   Mejorado, Lupe H ^a   Pettus, Thomas R R ^a  

^a UNIVERSITY OF CALIFORNIA   (United States)

Author keywords

Asymmetric 4+2 cycloaddition; Benzopyran; Benzylic stereocenter; Chiral enol ethers; Chroman; Diels Alder; Inverse demand; Lactol; o quinone methide; Total synthesis

Indexed keywords

BENZOPYRAN DERIVATIVE; CYCLOHEXANOL DERIVATIVE; ETHER DERIVATIVE; QUINONE DERIVATIVE;

ARTICLE; CHIRALITY; CYCLOADDITION; ENANTIOSELECTIVITY; REACTION ANALYSIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 3142771836     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2004-822888     Document Type: Article

References (30)

1. (a) Van De Water, R.; Magdziak, D.; Chau, J.; Pettus, T. R. R. J. Am. Chem. Soc. 2000, 122, 6502.
2. (b) Jones, R. M.; Selenski, C.; Pettus, T. R. R. J. Org. Chem. 2002, 67, 6911.
3. (a) Posner, G.; Wettlaufer, D. G. Tetrahedron Lett. 1986, 27, 667.
4. (b) Choudhury, A.; Franck, R. W.; Gupta, R. B. Tetrahedron Lett. 1989, 30, 4921.
5. (c) Denmark, S. E.; Schnute, M. E.; Marcin, L. R.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
6. (d) Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1996, 37, 4007.
7. (e) Prapansiri, V.; Thornton, E. R. Tetrahedron Lett. 1991, 32, 3147.
8. (a) Bissel, P.; Nazih, A.; Sablong, R.; Lepoittevin, J.-P. Org. Lett. 1999, 1, 1283.
9. (b) Johnson, S. J.; Evans, D. A. Acc. Chem. Res. 1999, 33, 325.
10. Tuttle, K.; Rodriguez, A. A.; Pettus, T. R. R. Synlett 2003, 2234.
11. Fullas, F.; Kornberg, L. J.; Wani, M. C.; Wall, M. E. J. Nat. Prod. 1996, 59, 190.
12. (a) Chavez, D. E.; Jacobsen, E. N. Org. Lett. 2003, 5, 2563.
13. (b) Juhl, K.; Jorgensen, K. A. Angew. Chem. Int. Ed. 2003, 42, 1498.
14. (a) Watanabe, W. H.; Conlon, L. W. J. Org. Chem. 1957, 79, 2828.
15. (b) Dujardin, G.; Rossignol, S.; Brown, E. Tetrahedron Lett. 1995, 36, 1653.
16. Okimoto, Y.; Sakaguchi, S.; Ishii, Y. J. Am. Chem. Soc. 2002, 124, 1590.
17. (a) Denmark, S. E.; Schnute, M. E.; Marcin, L. R.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
18. (b) Denmark, S. E.; Marcin, L. R.; Schnute, M. E.; Thorarensen, A. J. Org. Chem. 1995, 60, 3205.
19. 3): δ 153.3, 152.2, 150.2, 144.5, 128.3, 128.2, 128.0, 126.5, 125.4, 113.6, 110.2, 100.7, 83.9, 51.7, 35.5, 34.9, 33.0, 29.9, 27.9, 27.8, 26.0, 25.5, 21.4. Compound 9: See ref. 13.
20. Demyttenaere, J.; Van Syngel, K.; Peter Markusse, A.; Vervisch, S.; Debenedetti, S.; De Kimpe, N. Tetrahedron 2002, 55, 2163.
21. 6Si: 368; found: 368.
22. 4Si: 530.7697; found: 530.2835.
23. 3): δ 7.34-7.20 (m, 5 H), 6.43 (s, 1 H), 6.26 (s, 1 H), 5.60-5.58 (m, 1 H), 4.27-4.23 (m, 1 H), 4.08 (t, J = 8.5 Hz, 2 H), 3.59 (s, 3 H), 2.29-2.23 (m, 1 H), 2.17-2.06 (m, 1 H), 1.23-1.21 (t, 7 = 8.5 Hz, 2 H), 0.07 (s, 2 H).
24. 4Si: 388.5726; found: 388.2083.
25. Miki, Y.; Hachiken, H.; Nogurchi, K.; Ohta, M.; Nakano, A.; Takahashi, N.; Takemura, S. Chem. Pharm. Bull. 1990, 38, 3257.
26. Cohen, N.; Weber, G. F. Hoffmann-La Roche F. & Co. A.-G. Switzerland Eur. Pat. Appl. EP 84107289, 19840625, 1985, 109.
27. (a) Ku, Y.-Y.; Grieme, T.; Raje, P.; Sharma, P.; Morton, H. E.; Rozema, M.; King, S. A. J. Org. Chem. 2003, 68, 3238.
28. (b) Fontana, E.; Vicario, G. P.; Melloni, P. J. Labelled Compd. Radiopharm. 1989, 27, 1035.
29. Botteghi, C.; Corrias, T.; Marchetti, M.; Paganelli, S.; Piccolo, O. Org. Process Res. Dev. 2002, 6, 379.
30. Macas, F. A.; Varela, R. M.; Torres, A.; Molinillo, J. M. G. Tetrahedron Lett. 1999, 40, 4725.