Process for the manufacture of (6E)-leukotriene B.sub.4 and inte

Details Process for the manufacture of (6E)-leukotriene B.sub.4 and inte Process for the manufacture of (6E)-leukotriene B.sub.4 and inte

1993-07-20

1994-03-08

Prescott, Arthur C.

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

Organic compounds

Fatty compounds having an acid moiety which contains the...

554126, 554141, 554145, 554146, 554148, 549214, 549273, 556427, 556444, 568 23, 568852, 568857, C07C 5109, C07C 3118, C07D30900

Patent

active

052929078

ABSTRACT:
The invention relates to a process for the manufacture of 6-trans-leukotriene B.sub.4 (LTB.sub.4) of formula ##STR1## in which a butadienediol is prepared; the hydroxyl groups are esterified to produce a diester and this diester is subjected to a stereospecific reductive elimination using low valency titanium [Ti(0)] to produce a 6-trans triether of formula: ##STR2## the groups --OA in positions 5 and 12 of which are then converted to --OH groups and the group --CH.sub.2 OA in position of which is then converted to a --COOH group, to produce 6-trans-LTB.sub.4.
The invention also relates to intermediates obtained in the said manufacturing process.

REFERENCES:
patent: 4873024 (1989-10-01), Abe et al.
patent: 5110949 (1992-05-01), Abe et al.
Green et al, "Natural acetylenes. Part 59. Synthesis of (-)-(E,S)-dodec-4-ene-6,8,10-triyn-3-ol, the enantiomer of a metabolite of the fungus Peniophora resinosa Jackson and Dearden.", Chem. Abstracts vol. 103, 1985, 141711g.

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