Synthesis of (E,Z)-5-bromo-1,1-dimethoxy-5-trimethylsilyl-4-pentene, an upper chain allenic prostaglandin building block

Synthetic Communications

Volumn 33, Issue 19, 2003, Pages 3271-3283

  Guzmán Durán, Antonio ^a   Guzmán, Esther ^b   Pannell, Keith H ^c   Lloyd, Winston D ^c  

^a Contributio Ctro Invest Mat A ^*  (Mexico)

^b UNIVERSITY OF TEXAS   (United States)

^c UNIVERSITY OF TEXAS AT EL PASO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

1,1 DIMETHOXY 6 PHENYL 1,4,5 HEXADIENE; 5 BROMO 1,1 DIMETHOXY 5 TRIMETHYLSILYL 4 PENTENE; ALLENE DERIVATIVE; LUTEOLYTIC AGENT; PROSTAGLANDIN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; HYDROLYSIS; ISOMER; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; RELIABILITY; THIN LAYER CHROMATOGRAPHY;

EID: 18344402128     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120023984     Document Type: Article

References (27)

1. Barret, P.; Barreiro, E.; Greene, A.E.; Luche, J.L.; Texeira, M.A.; Crabbe, P. Tetrahedron 1979, 35, 2931.
2. Crabbe, P.; Carpio, H. J. Chem. Soc. Commun. 1972, 904.
3. Freid, J.H.; Muchowski, J.M.; Carpio, H. Prostaglandins 1977, 14, 807.
4. Corey, E.J.; Albocino, S.M.; Koelliker, U.; Schoaf, T.K.; Varma, R.K. J. Am. Chem. Soc. 1971, 93, 1491.
5. Tomoskozi, I.; Gruber, L.; Kovacs, G.; Szekely, I.; Simonidesz, V. Tetrahedron Lett. 1976, 50, 4639.
6. Corey, E.J.; Weinshenker, N.M.; Schaaf, T.K.; Huger, W. J. Am. Chem. Soc. 1969, 91, 5675.
7. Corey, E.J.; Schaaf, T.K.; Hugar, W.; Koelliker, U.; Weinshenker, N.M. J. Am. Chem. Soc. 1970, 92, 397.
8. Corey, E.J.; Bakshi, R.K.; Shibata, S.; Chen, S.; Singh, V.K. J. Am. Chem. Soc. 1987, 109, 7925.
9. Zweifel, G.; Lewis, W. J. Org. Chem. 1978, 43, 2739.
10. Lynd, R.A.; Zweifel, G. Synthesis 1974, 658.
11. Eisch, J.J.; Foxton, M.W. J. Organomet. Chem. 1968, 11, 24.
12. Eisch, J.J.; Damasevitz, G.A. J. Org. Chem. 1976, 41, 2214.
13. Negishi, E.; Baba, S.I.; King, A.O. J. Chem. Soc., Chem. Commun. 1976, 17.
14. Baba, S.; Van Hom, D.E.; Negishi, E. Tetrahedron Lett. 1976, 23, 1927.
15. Peterson, D.J. J. Org. Chem. 1968, 33, 780.
16. Miller, R.B.; McGarvey, G. J. Org. Chem. 1979, 44, 4623.
17. Newmann, H.; Seebach, D. Tetrahedron Lett. 1976, 52, 4839.
18. Zweifel, G.; Murray, R.E.; On, H.P. J. Org. Chem. 1981, 46, 1292.
19. Chan, T.H. Acc. Chem. Res. 1977, 10, 442.
20. Chan, T.H.; Ong, B.S.; Mychajlowskij, W. Tetrahedron Lett. 1976, 37, 3253.
21. Ong, B.S.; Chan, T.H. Tetrahedron Lett. 1976, 37, 3257.
22. Hudrlik, P.F.; Peterson, D. J. Am. Chem. Soc. 1975, 97, 1464.
23. (a) Shaw, B.L.; Whiting, M.C. J. Chem. Soc. 1954, 3217;
24. (b) Eglenton, G.; Whiting, M.C. J. Chem. Soc. 1950, 3651.
25. On, H.P.; Lewis, W.; Zweifel, G. Synthesis 1981, 999.
26. Just, G.; Luthe, C. Tetrahedron Lett. 1982, 23, 1331.
27. Corey, E.J.; Kang, M.; Desai, M.C.; Ghosh, A.K.; Houpis, I.N. J. Am. Chem. Soc. 1988, 110, 649.