Stereoselective syntheses of the antihistaminic drug olopatadine and its E-isomer.
Practical stereoselective synthetic routes to the antihistaminic drug olopatadine and its E-isomer have been developed, the key steps being a trans stereoselective Wittig olefination using a nonstabilized phosphorus ylide and a stereoselective Heck cyclization. The stereoselectivity of the Wittig reaction depends on both the phosphonium salt anion and the cation present in the base used to generate the ylide.
Laboratory of Organic Chemistry, Faculty of Pharmacy, and Institute of Biomedicine (IBUB), University of Barcelona, Av. Joan XXIII s/n, 08028 Barcelona, Spain. joanbosch@ub.edu
Joan
J
Bosch
Jordi
J
Bachs
Antonia M
AM
Gómez
Rosa
R
Griera
Marta
M
Écija
Mercedes
M
Amat
D003500:Cyclization; D003990:Dibenzoxepins / Q000138:chemical synthesis* / Q000737:chemistry; D006633:Histamine Antagonists / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D000069605:Olopatadine Hydrochloride; D013237:Stereoisomerism
D003990:Dibenzoxepins; D006633:Histamine Antagonists; D000069605:Olopatadine Hydrochloride