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A Facile Route for Synthesis of (±)-Dinoprost, (±)-Carboprost and Its Analogs
Corresponding Author(s) : M. Shankar
Asian Journal of Chemistry,
Vol. 25 No. 2 (2013): Vol 25 Issue 2
Abstract
A general synthetic approach was developed for (±)-dinoprost (1), (±)-carboprost (2) and their analogs (3-5) through a key intermediate (6). Compound 6 can be converted into the target compounds in two or three steps. Diastereomeric separation was accomplished easily for obtaining (±) dinoprost. Separation of diastereomers was difficult for (±) carboprost and their analogs. Key intermediate 6 was obtained, in turn, from (±)-corey lactone.
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- S. Bergstrom, Science, 157, 382 (1967).
- Prostaglandins in Proceedings of the Second Nobel Symposium, Stockholm, June, (1966), S. Bergstrom and B. Samuelsson, Almquist and Wiksell, Gebers Forlag AB, Stockholm (1967).
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References
S. Bergstrom, Science, 157, 382 (1967).
Prostaglandins in Proceedings of the Second Nobel Symposium, Stockholm, June, (1966), S. Bergstrom and B. Samuelsson, Almquist and Wiksell, Gebers Forlag AB, Stockholm (1967).
J.R. Weeks, Ann. Rev. Pharmacol., 12, 317 (1972).
J.W. Hinman, Ann. Rev. Biochem., 41, 161 (1972).
B. Samuelsson, K. Granstrom, GrCen, M. Hamberg, Ann. N.Y. Acad. Sci., 180, 138 (1971).
B. Samuelsson, Aduan. Biosci., 9, 7 (1973).
E. AnggHrd and B. Samuelsson, Ark. Kemi, 25, 293 (1966).
M. Harikrishna, H. Rama Mohan, P.K. Dubey, M. Shankar and G.V. Subbaraju, Asian J. Chem., 23, 3121 (2011).
W. Lippmann, Ann. N. Y. Acad. Sci., 180, 332 (1971).
P.W. Collins and S.W Djuric, Chem. Rev., 93, 1533 (1993).
V. Hingorani and A. Dua, Department of Obstetrics and Gynaecology, All India Institute of Medical Sciences, vol. 39, B. No. 3. New Delhi, India.
J. Brenner, T. Fishburne, Braaksma and C.H. Hendricks, Obstet. Gynec., 39, 892 (1972).
M. Sakurai, M. Araie, T. Oshika, M. Mori, K. Masuda, R. Ueno and M. Takase, Jpn. J. Ophthalmol., 35, 156 (1991).
B. Resul, J. Stjernschantz, K. No, C. Liljebris, G. Selen, M. Astin, M. Karlsson and L.Z. Bito, J. Med. Chem., 36, 243 (1993).
P.A. Netland, T. Landry, E.K. Sullilvan, R. Andrew, L. Silver, A. Weiner, S. Mallick, J. Dickerson, M.V. Bergamini, S.M. Robertson and A.A. Davis, Am. J. Ophthalmol., 132, 472 (2001).
R.F. Brubaker, E.O. Schoff, C.B. Nau, S.P. Carpenter, K. Chen and A.M. Vandenburgh, Am. J. Ophthalmol., 131, 19 (2001).
M. Harikrishna, H.R. Mohan, P.K. Dubey, M. Shankar and G.V. Subbaraju, Synth. Commun., 42, 1288 (2012)
M. Harikrishna, H.R. Mohan, P.K. Dubey, M. Shankar, G.V. Subbaraju and T. Lakshmikumar, Lett. Org. Chem., 8, 234 (2011).
M. Harikrishna, H.R. Mohan, P.K. Dubey, M. Shankar and G.V. Subbaraju, Asian J. Chem., 23, 3121 (2011).
W.Y. Ernest, A. Udo and L.B. Gordon, J. Am. Chem. Soc., 96, 5865 (1974).
C. Earil and W.Y. Ernest, J. Am. Chem. Soc., 96, 5876 (1974).
P.W. Collins and S.W. Djuric, Chem. Rev., 93, 1533 (1993).
S. Das, S. Chandrasekhar, J.S. Yadav and G. Rane, Chem. Rev., 107, 3286 (2007).
B. Helferich and W. Schaefer, Org. Synth. Coll., 1, 147 (1941).
J. Avila-Zarraga, R. Gustavo, Martinez, Synth. Commun., 31, 2177 (2001).
F. Mathey and P. Savignac, Tetrahedron, 34, 649 (1978).
I. Martin, J. Anvelt, T. Valimae, T. Pehk and O. Lille, Synth. Commun., 20, 2597 (1990).
S.W. Hwang, M. Adiyaman, S. Khanapure, L. Schio and J. Rokach, J. Am. Chem. Soc., 116, 10829 (1994).
B. Resul, J. Stjernschantz, K. No, C. Liljebris, G. Selen, M. Astin, M. Karlsson and L.Z. Bito, J. Med. Chem., 36, 243 (1993).
G.Q. Long and K.C. Jin, J. Am. Chem. Soc., 124, 12424 (2002).
A. Neil, Sheddan and M. Johann, Org. Lett., 8, 3101 (2006).
S.R. Ruben, G. Sylvain, M.Z.S. Alexandra, P. Alessio, D.A. Alessandro, Z. Giuseppe and P.N. Steven, Organometallics, 29, 3665 (2010).
A.S. Neil, B.A. Vladimir and M. Johann, Tetrahedron Lett., 47, 6689 (2006).
M. Shizuka and M.L. Snapper, Synthesis, 2397 (2007).
C.B. Francisco, R.R. Alessandra and C.F.S. Marcela, Lett. Org. Chem., 4, 1 (2007).
K. Weinges, W. Huber, U. Huber-Patz, H. Irngartinger, M. Nixdorf and H. Rodewald, Liebigs Ann. Chem., 4, 761 (1984).
G.L. Bundy, D.C. Peterson, J. C. Cornette, W.L. Miller, C.H. Spilman and J.W. Wilks, J. Med. Chem., 26, 1089 (1983).
Astrazeneca Pharma India Limited, Astrazeneca UK Limited, WO2008/ 81191 (2008).
L.B. Gordon and M. Kalamazoo, U.S. Patent, 3804890 (1974).
L.B. Gordon and M. Portage, U.S. Patent, 3904679 (1975).