Chelation-control in the formal [3+3] cyclization of 1,3-bis-(silyloxy)-1,3-butadienes with 1-hydroxy-5-silyloxy-hex-4-en-3-ones. One-pot synthesis of 3-aryl-3,4-dihydroisocoumarins

Tetrahedron

Volumn 66, Issue 10, 2010, Pages 1874-1884

  Ullah, Ihsan ^a,b   Sher, Muhammad ^a,b,c   Khera, Rasheed Ahmad ^a   Ali, Asad ^a,b   Ibad, Muhammad Farooq ^a   Villinger, Alexander ^a   Fischer, Christine ^b   Langer, Peter ^a,b  

^a UNIVERSITY OF ROSTOCK   (Germany)

^b LEIBNIZ INSTITUT FÜR KATALYSE E V AN DER UNIVERSITÄT ROSTOCK   (Germany)

^c ALLAMA IQBAL OPEN UNIVERSITY   (Pakistan)

Author keywords

Arenes; Cyclizations; Isocoumarins; Regioselectivity; Silyl enol ethers

Indexed keywords

1,3 BUTADIENE DERIVATIVE; 3 (2 FLUOROPHENYL) 8 HYDROXY 6 METHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (2 FLUOROPHENYL) 8 HYDROXY 6,7 DIMETHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (2,3 DIMETHOXYPHENYL) 8 HYDROXY 6 METHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (2,3 DIMETHOXYPHENYL) 8 HYDROXY 6,7 DIMETHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (4 CHLOROPHENYL) 7 ETHYL 8 HYDROXY 6 METHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (4 CHLOROPHENYL) 7 HEXYL 8 HYDROXY 6 METHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (4 CHLOROPHENYL) 8 HYDROXY 6 METHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (4 CHLOROPHENYL) 8 HYDROXY 6,7 DIMETHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 3 (4 ETHYLPHENYL) 8 HYDROXY 6 METHYL 3,4 DIHYDROISOCHROMAN 1 ONE; 7 (BUT 3 ENYL) 8 HYDROXY 6 METHYL 3 (4 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 7 (BUT 3 ENYL) 8 HYDROXY 6 METHYL 3 PHENYL 3,4 DIHYDROISOCHROMAN 1 ONE; 7 ALLYL 8 HYDROXY 6 METHYL 3 (4 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 7 BUTYL 8 HYDROXY 6 METHYL 3 (4 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 7 DECYL 8 HYDROXY 6 METHYL 3 PHENYL 3,4 DIHYDROISOCHROMAN 1 ONE; 7 ETHYL 8 HYDROXY 6 METHYL 3 (3 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 7 ETHYL 8 HYDROXY 6 METHYL 3 PHENYL 3,4 DIHYDROISOCHROMAN 1 ONE; 7 HEXYL 8 HYDROXY 6 METHYL 3 (3 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 7 HEXYL 8 HYDROXY 6 METHYL 3 PHENYL 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6 METHYL 3 (3 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6 METHYL 3 (PYRID 4 YL) 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6 METHYL 3 4 TOLYL 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6 METHYL 3 PHENYL 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6 METHYL 7 NONYL 3 PHENYL 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6 METHYL 7 PHENETHYL 3 (4 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6,7 DIMETHYL 3 (3 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6,7 DIMETHYL 3 (4 TOLYL) 3,4 DIHYDROISOCHROMAN 1 ONE; 8 HYDROXY 6,7 DIMETHYL 3 PHENYL 3,4 DIHYDROISOCHROMAN 1 ONE; ISOCOUMARIN DERIVATIVE; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHELATION; CRYSTAL STRUCTURE; CYCLIZATION; DRUG STRUCTURE; LACTONIZATION; ONE POT SYNTHESIS; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE;

EID: 75849154990     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2010.01.019     Document Type: Article

References (28)

1. Zhang H., Matsuda H., Kumahara A., Ito Y., Nakamura S., and Yoshikawa M. Bioorg. Med. Chem. Lett. 17 (2007) 4972
2. Shimoda H., Matsuda H., Yamahara J., and Yoshikawa M. Biol. Pharm. Bull. 21 (1998) 809
3. Patnam R., Chang F.-R., Chen C.-Y., Kuo R.-Y., Lee Y.-H., and Wu Y.-C. J. Nat. Prod. 64 (2001) 948
4. Yasuda T., Kayaba S., Takahashi K., Nakazawa T., and Ohsawa K. J. Nat. Prod. 67 (2004) 1604
5. Nozawa K., Yamada M., Tsuda Y., Kawai K.-I., and Nakajima S. Chem. Pharm. Bull. 29 (1981) 2689
6. Wang Q., Matsuda H., Matsuhira K., Nakamura S., Yuan D., and Yoshikawa M. Biol. Pharm. Bull. 30 (2007) 388
7. Matsuda H., Shimoda H., Yamahara J., and Yoshikawa M. Biol. Pharm. Bull. 22 (1999) 870
8. Kawamura M., Kagata M., Masaki E., and Nishi H. Pharmacol. Toxicol. (Copenhagen) 90 (2002) 106
9. Umehara K., Matsumoto M., Nakamura M., Miyase T., Kuroyanagi M., and Noguchi H. Chem. Pharm. Bull. 48 (2000) 566
10. Matsuda H., Shimoda H., Yamahara J., and Yoshikawa M. Bioorg. Med. Chem. Lett. 8 (1998) 215
11. Yoshikawa M., Matsuda H., Shimoda H., Shimada H., Harada E., Naitoh Y., Miki A., Yamahara J., and Murakami N. Chem. Pharm. Bull. 44 (1996) 1440
12. Yoshikawa M., Harada E., Naitoh Y., Inoue K., Matsuda H., Shimoda H., Yamahara J., and Murakami N. Chem. Pharm. Bull. 42 (1994) 2225
13. Yoshikawa M., Uchida E., Chatani N., Kobayashi H., and Naitoh Y. Chem. Pharm. Bull. 40 (1992) 3352
14. Hashimoto T., Tori M., and Asakawa Y. Phytochemistry 26 (1987) 3323
15. Matsuda H., Shimoda H., and Yoshikawa M. Bioorg. Med. Chem. 7 (1999) 1445
16. Chan T.-H., and Brownbridge P. J. Am. Chem. Soc. 102 (1980) 3534
17. Brownbridge P., Chan T.-H., Brook M.A., and Kang G.J. Can. J. Chem. 61 (1983) 688
18. For a review of [3+3] cyclizations, see:. Feist H., and Langer P. Synthesis (2007) 327
19. For a review of 1,3-bis(silyl enol ethers), see:. Langer P. Synthesis (2002) 441
20. Nguyen V.T.H., and Langer P. Tetrahedron Lett. 46 (2005) 1013
21. Hussain I., Nguyen V.T.H., Yawer M.A., Dang T.T., Fischer C., Reinke H., and Langer P. J. Org. Chem. 72 (2007) 6255
22. Sher M., Ali A., Reinke H., and Langer P. Tetrahedron Lett. 49 (2008) 5400
23. For reviews of domino reactions, see:
24. Tietze L.F., and Beifuss U. Angew. Chem., Int. Ed. Engl. 32 (1993) 131
25. Angew. Chem. 105 (1993) 137
26. Tietze L.F. Chem. Rev. 96 (1996) 115
27. Weiler L. J. Am. Chem. Soc. 92 (1970) 6702
28. CCDC 756025-756028 contain all crystallographic details of this publication and is available free of charge at www.ccdc.cam.ac.uk/conts/retrieving.html or can be ordered from the following address: Cambridge Crystallographic Data Centre, 12 Union Road, GB-Cambridge CB21EZ; Fax: (+44) 1223-336-033; or deposit@ccdc.cam.ac.uk.