Method of synthesizing leukotriene B.sub.4 and derivatives there

Details Method of synthesizing leukotriene B.sub.4 and derivatives there Method of synthesizing leukotriene B.sub.4 and derivatives there

1989-09-13

1992-05-05

Chan, Nicky

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

549415, 549416, 549420, 549423, C07D30912

Patent

active

051109492

ABSTRACT:
An improved method for synthesizing leukotriene B.sub.4 and derivatives thereof is disclosed, as are novel intermediates used in the process. Unlike prior art processes, the method of this invention involves a step in which 2(R)-[[(1,1-dimethylethyl)diphenylsilyl]oxy]dec-4 (Z)-ene-1-ol or a related compound is coupled with methyl-[5(S)-[[1,1dimethylethyl)-diphenylsilyl]oxy]-dec-8 (E)-10-(dimethylphosphono)-6-ynoate.

REFERENCES:
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Nicolaon et al., JCS, Chem. Comm., 1982, (22), 1292-3.
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Corey, E. J., Marfat, A., Goto, G., Brion, F., J. Am. Chem. Soc., 102, 7986 (1980).
Corey, E. J., Marfat, A., Munroe, J., Kim, K. S., Hopkins, P. B., Brion, F., Tetrahedron Lett., 22, 1077 (1981).
Guindon, Y., Zamboni, R., Lau, C.-K., Rokach, J., Tetrahedron Lett., 23, 739-742, (1981).
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Mills, L. S., North, P. C., Tetrahedron Lett., 24, 409 (1983).
Nicolaou, K. C., et al., "A General and Stereocontrolled Total Synthesis of Leukotriene B.sub.4 and Analogues," J. Am. Chem. Soc., 106, 3748-3551 (1984).

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