Bioorganic and Medicinal Chemistry Letters p. 1787 - 1790 (1998)
Update date:2022-08-03
Topics:
Chambers
Koch
Biggers
Ramchandani
Structural modification of 1 led to a series of 2-(4-hydroxy-7- chromanyl)benzoic acid LTB4 antagonists exemplified by 2 and 3. The use of an organostannane biaryl coupling, a non stereoselective reduction and a chromatographic resolution limited the utility of this synthetic route. To address these issues, a new synthetic route was developed utilizing a palladium catalyzed coupling of aryl oxazolines in tandem with a stereospecific enone reduction as key synthetic steps. Resolution was achieved by fractional crystallization of a (S)-(-)-α-methylbenzylamine salt.
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