A New Synthetic Approach to Prostaglandin Analogues: Synthesis of Bimatoprost via Lipase Enzymatic Catalysis

Vijendhar Kamidi; Pooja Kale; Sathyanarayana Boodida

doi:10.14233/ajchem.2017.20878

Issue

Vol. 29 No. 12 (2017): Vol 29 Issue 12

Issue Published : October 30, 2017

This work is licensed under a Creative Commons Attribution 4.0 International License.

A New Synthetic Approach to Prostaglandin Analogues: Synthesis of Bimatoprost via Lipase Enzymatic Catalysis

https://doi.org/10.14233/ajchem.2017.20878

Vijendhar Kamidi

Department of Chemistry, JNTUH College of Engineering Jagtial, Karimnagar-505 501, India

Pooja Kale

R & D Division, Matrica Laboratories Ltd, Nacharam, Hyderabad-500 008, India

Sathyanarayana Boodida

Department of Chemistry, JNTUH College of Engineering Jagtial, Karimnagar-505 501, India

Corresponding Author(s) : Sathyanarayana Boodida

bs14@jntuh.ac.in

Asian Journal of Chemistry, Vol. 29 No. 12 (2017): Vol 29 Issue 12
Article Published : October 31, 2017

Abstract

A simple, convenient and efficient synthetic approach for the synthesis of (15S) bimatoprost (4) via lipase enzyme mediated stereo selective reduction from chiral precursor Corey lactone diol as substrate was described. Swern oxidation, lipase enzymatic reduction and Wittig reaction conditions are used as key steps for the synthesis of bimatoprost. This method was found to be an efficient with considerable yield, cost effective and minimized the synthetic steps compared to reported procedures.

Keywords

Prostaglandins Bimatoprost Lipase enzymatic reduction Corey lactone diol

Kamidi, V., Kale, P., & Boodida, S. (2017). A New Synthetic Approach to Prostaglandin Analogues: Synthesis of Bimatoprost via Lipase Enzymatic Catalysis. Asian Journal of Chemistry, 29(12), 2767–2770. https://doi.org/10.14233/ajchem.2017.20878

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References

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Allergan gets FDA approval, Business Week, Associated Press (2008).
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K.M. Maloney and J.Y.L. Chung, J. Org. Chem., 74, 7574 (2009); https://doi.org/10.1021/jo901552k.
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K. Vijendhar, B. Srinivas and S. Boodida, J. Chem. Sci., 127, 2023 (2015); https://doi.org/10.1007/s12039-015-0963-2.

References

D. De Souza, M. Albert and H. Sturn, Improved Process for the Production of Bimatoprost, US Patent US2011/0178340 A1 (2011).

H. Mudduluru, R. M. Hindupur, P. K. Dubey, S. Madhavaram, L. Tatini and G. V. Subbaraju, Lett. Org. Chem., 8, 234 (2011); https://doi.org/10.2174/157017811795371485.

M.R. Hellberg, R.E. Conrow, N.A. Sharif, M.A. McLaughlin, J.E. Bishop, J.Y. Crider, W.D. Dean, K.A. De Wolf, D.R. Pierce, V.L. Sallee, R.D. Selliah, B.S. Severns, S.J. Sproull, G.W. Williams, P.W. Zinke and P.G. Klimko, Bioorg. Med. Chem., 10, 2031 (2002); https://doi.org/10.1016/S0968-0896(02)00016-0.

P. Klimko, M. Hellberg, M. McLaughlin, N. Sharif, B. Severns, G. Williams, K. Haggard and J. Liao, Bioorg. Med. Chem., 12, 3451 (2004); https://doi.org/10.1016/j.bmc.2004.04.034.

G. Zanoni,A. D’Alfonso,A. Porta, L. Feliciani, S.P. Nolan and G. Vidari, Tetrahedron, 66, 7472 (2010); https://doi.org/10.1016/j.tet.2010.07.069.

Z. Feng, M.R. Hellberg, N.A. Sharif, M.A. McLaughlin, G.W. Williams, D. Scott and T. Wallace, Bioorg. Med. Chem., 17, 576 (2009); https://doi.org/10.1016/j.bmc.2008.11.070.

Allergan gets FDA approval, Business Week, Associated Press (2008).

A.K. Macharla, R. Chozhiyath Nappunni, M.R. Marri, S. Peraka and N. Nama, Tetrahedron Lett., 53, 191 (2012); https://doi.org/10.1016/j.tetlet.2011.11.011.

K.M. Maloney and J.Y.L. Chung, J. Org. Chem., 74, 7574 (2009); https://doi.org/10.1021/jo901552k.

M.R. Marri, A.K. Macharla, S. Peraka and N. Nama, Tetrahedron Lett., 52, 6554 (2011); https://doi.org/10.1016/j.tetlet.2011.09.106.

M.T. Maghsoodlou, S.M.H. Khorassani, M.K. Rofouei, S.R. Adhamdoust and M. Nassiri, ARKIVOC, 145 (2006); https://doi.org/10.3998/ark.5550190.0007.c17.

K. Vijendhar, B. Srinivas and S. Boodida, J. Chem. Sci., 127, 2023 (2015); https://doi.org/10.1007/s12039-015-0963-2.

Issue

Vol. 29 No. 12 (2017): Vol 29 Issue 12

A New Synthetic Approach to Prostaglandin Analogues: Synthesis of Bimatoprost via Lipase Enzymatic Catalysis

Corresponding Author(s) : Sathyanarayana Boodida

Abstract

Keywords

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