Abstract
An efficient asymmetric synthetic route for the synthesis of anti-glaucoma agent, (15R)-latanoprost using Corey lactone diol as chiral substrate under Swern oxidation, allylic reduction and Wittig reaction conditions has been developed. In this method, reduction of keto and alkene functional groups has been achieved in a single step using low cost catalyst NiCl2/NaBH4 in methanol. This new synthetic protocol is a good alternative for the synthesis of latanoprost with high stereo selectivity and improved yield.
A simple, convenient and convergent approach for the synthesis of (15R) latanoprost is reported with high stereo selectivity and improved yield from chiral precursor Corey lactone diol using Swern oxidation, allylic reduction and Wittig reaction conditions.
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One of the authors KV is grateful to the Aspen Bio Pharma Labs Pvt. Ltd for providing research opportunity to carry out his research program.
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The supplementary information pertaining to characterization of the synthesized compounds using 1H NMR spectra (figures S1-S7), 13C NMR spectra (figures 8-12), IR spectra (figures 13) HPLC chromatogram (figure 14), Mass spectra (figure S15) and SOR spectrum data (table S15) are available at www.ias.ac.in/chemsci.
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VIJENDHAR, K., SRINIVAS, B. & BOODIDA, S. A Facile and Efficient Synthesis of (15R)-Latanoprost from Chiral Precursor Corey Lactone Diol. J Chem Sci 127, 2023–2028 (2015). https://doi.org/10.1007/s12039-015-0963-2
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DOI: https://doi.org/10.1007/s12039-015-0963-2