AN EFFICIENT AND LABORATORY FRIENDLY SYNTHESIS OF ANTI-GLAUCOMA AGENT OF BIMATOPROSTAbstract
An alternative, economically viable, and laboratory-friendly synthetic method described for the preparation of Bimatoprost, an anti-glaucoma drug. Stereospecific synthesis of Bimatoprost has been achieved with commercially available (-) Corey lactone i.e., diol, as a starting material. To our delight, the replacement of the benzoyl (Bz) group with Tetrahydropyranyl ether (Thp) protection resulted in yield improvement. Tetrahydropyranyl ether (Thp) is notorious as a useful protecting group for alcohols in organic synthesis. It has numerous benefits, such as low cost, ease of insertion, general stability to most non-acidic conditions. It offers good solubility and easy to remove if the functional group it protects requires manipulation. Moreover, it described the successful application of luche’s reduction for the conversion of α, β-unsaturated ketone 8 to allylic alcohol 9 using CeCl3 7H2O, NaBH4. This lanthanide combination with borohydride enables the selective 1, 2-hydride attack on the carbonyl group, instead of an undesired 1, 4-hydride attack, which leads to the formation of desired allylic alcohol without disturbing the double bond.
R. M. R. Jaggavarapu, M. Venkatanarayana *, G. V. Reddy and K. K. Gudimella
Department of Chemistry, Gitam School of Science, GITAM (Deemed to be University), Hyderabad, Telangana, India.
30 April 2020
04 September 2020
11 September 2020
01 May 2021