Synthesis of 4-hydroxy- and 2,4-dihydroxy-homophthalates by [4+2] cycloaddition of 1,3-bis(silyloxy)-1,3-butadienes with dimethyl allene-1,3-dicarboxylate

Tetrahedron

Volumn 64, Issue 34, 2008, Pages 8003-8009

  Hussain, Ibrar ^a   Yawer, Mirza A ^a   Appel, Bettina ^a   Sher, Muhammad ^a,b   Mahal, Ahmed ^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)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BIS(SILYLOXY) 1,3 BUTADIENE; 1,3 BUTADIENE; 2,4 DIHYDROXY HOMOPHTHALATE; 4 HYDROXY HOMOPHTHALATE; CARBOXYLIC ACID DERIVATIVE; DIMETHYL ALLENE 1,3 DICARBOXYLATE; METHYL 2,4 DIHYDROXY 6 (METHOXYCARBONYLMETHYL) BENZOATE; PHTHALIC ACID;

ARTICLE; CHEMICAL REACTION; CYCLOADDITION; PRIORITY JOURNAL; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 46649093949     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.05.118     Document Type: Article

References (22)

1. In: Krause N., and Hashmi A.S.K. (Eds). Modern Allene Chemistry (2004), Wiley-VCH, Weinheim 760-787
2. Fink M., Gaier H., and Gerlach H. Helv. Chim. Acta 65 (1982) 2563
3. Hayakawa K., Nishiyama H., and Kanematsu K. J. Org. Chem. 50 (1985) 512
4. Roush W.R., and Murphy M. J. Org. Chem. 57 (1992) 6622
5. Langer P., and Kracke B. Tetrahedron Lett. 41 (2000) 4545
6. Cox C.D., Siu T., and Danishefsky S.J. Angew. Chem., Int. Ed. 42 (2003) 5625
7. Rech J.C., and Floreancig P.E. Org. Lett. 7 (2005) 5175
8. Kim S., Fan G.-J., Lee J., Lee J.J., and Kim D. J. Org. Chem. 67 (2002) 3127
9. Chan T.-H., and Brownbridge P. J. Am. Chem. Soc. 102 (1980) 3534
10. Molander G.A., and Cameron K.O. J. Am. Chem. Soc. 115 (1993) 830
11. For a review of 1,3-bis(silyl enol ethers), see:. Langer P. Synthesis (2002) 441
12. Bryson T.A., and Dolak T.M. Org. Synth. 57 (1977) 62
13. Hünig S., and Wehner G. Synthesis (1975) 180
14. Lee H.J., Lee J.H., Hwang B.Y., Kim H.S., and Lee J.J. J. Antibiot. 55 (2002) 552
15. Hargreaves J., Park J.-o., Ghisalberti E.L., Sivasithamparam K., Skelton B.W., and White A.H. J. Nat. Prod. 65 (2002) 7
16. Hussein S.A.M., Ayoub N.A., and Nawwar M.A.M. Phytochemistry 63 (2003) 905
17. Nawwar M.A.M., Hussein S.A.M., Buddrus J., and Linscheid M. Phytochemistry 35 (1994) 1349
18. Fiedler P., Gambaro V., Garbarino J.A., and Quilhot W. Phytochemistry 25 (1986) 461
19. Lee S.-H., Tanaka T., Nonaka G.-i., and Nishioka I. Chem. Pharm. Bull. 39 (1991) 630
20. Yoshida T., Ahmed A.F., and Okuda T. Chem. Pharm. Bull. 41 (1993) 672
21. Elix J.A., Jones A.J., Lajide L., Coppins B.J., and James P.W. Aust. J. Chem. 37 (1984) 2349
22. CCDC-684863 (3b) contains all crystallographic details of this publication, which are 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.