European Journal of Chemistry

Studies towards the synthesis of (±)-reserpine: Photocyclization mediated a novel and efficient synthesis of 11,18-dimethoxy-(20α)-18,19-didehydro-yohimban-17-one

Article Sidebar

PDF
Published: Mar 31, 2012
DOI: https://doi.org/10.5155/eurjchem.3.1.26-31.503
Keywords:
Lactam, Reserpine, Harmaline, Total synthesis, Enamide photocyclization, Hypertension and mental disorders
Section
Research Article
Issue
Vol. 3 No. 1 (2012): March 2012
Dates
Received 2011-08-19
Accepted 2011-09-19
Published 2012-03-31


Main Article Content

Muhammad Yar
Interdisciplinary Research Center in Biomedical Materials, Comsats Institute of Information Technology, Lahore, 54000, Pakistan
Muhammad Arshad
Institute of Chemistry, University of the Punjab, Lahore, 54590, Pakistan
Muhammad Nadeem Akhtar
Laboratory of Natural Products, Institute of Bioscience, University Putra Malaysia, Serdang, Selangor Darul Ehsan, 43400, Malaysia
Sohail Anjum Shahzad
Department of Chemistry, Government College University, Lahore, 54000, Pakistan
Islam Ullah Khan
Department of Chemistry, Government College University, Lahore, 54000, Pakistan
Zulfiqar Ali Khan
Department of Chemistry, Government College University, Faisalabad, 38000, Pakistan
Nisar Ullah
Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia
Ichiya Ninomiya
International Center for Chemical and Biological Sciences, Hussain Ibrahim Jamal Research Institute of Chemistry, University of Karachi, Karachi, 75270, Pakistan

Abstract

A short, highly efficient synthesis of advanced intermediates to reserpine 1 has been developed starting from enamide 8. The enamide underwent photocyclization reaction using high pressure mercury lamp to afford the lactam 9 in excellent yield. Then lactam was reduced to the required amine 10, which upon acidic hydrolysis gave the nonconjugate ketone product 11, followed by reaction with sodium hydroxide resulted the desired conjugate ketone 12. Epoxidation, and then ring opening of the epoxide 13 with methanol yielded the desired product 14, which is key intermediate to the total synthesis of (±)-reserpine.

3_1_26_31_800


icon graph This Abstract was viewed 2268 times | icon graph Article PDF downloaded 804 times

How to Cite
(1)
Yar, M.; Arshad, M.; Akhtar, M. N.; Shahzad, S. A.; Khan, I. U.; Khan, Z. A.; Ullah, N.; Ninomiya, I. Studies towards the Synthesis of (±)-Reserpine: Photocyclization Mediated a Novel and Efficient Synthesis of 11,18-Dimethoxy-(20α)-18,19-Didehydro-Yohimban-17-One. Eur. J. Chem. 2012, 3, 26-31.

Article Details

Share
Links for Article


Crossref - Scopus - Google - European PMC
Crossref
Scopus
Google Scholar
Europe PMC
References

[1]. Muiler, J. M.; Schlittler, E.; Bein, H. J. Experientia 1952, 8, 338-339.
http://dx.doi.org/10.1007/BF02174406

[2]. Monachino, J. Econ. Bot. 1954, 8, 349-365.

[3]. Chatterjee, A.; Pakrashi, S.; Werner, G. Fortschr. Chem. Org. Naturst. 1956, 13, 346-351.

[4]. Woodson, R. E.; Younken, H. W.; Schlittler, E.; Schneider, J. A. Rauwolfia: Botany, Pharmacognosy, Chemistry, and Pharmacology, Little, Brown and Co., Boston, 1957.

[5]. Lucas, R. A. Prog. Med. Chem. 1963, 3, 146-186.
http://dx.doi.org/10.1016/S0079-6468(08)70118-8

[6]. Aube, J.; Ghosh, S. Advances in Heterocyclic Natural Product Synthesis; Pearson, W. H., Ed.; JAI (Java Advanced Imaging) Press: Greenwich, CT, 1996.

[7]. Szantay, C.; Honty, K. Monoterpenoid Indole Alkaloids; Saxton, J. E., Ed.; John Wiley & Sons, Chichester, 1994.

[8]. Baxter, E. W.; Mariano, P. S. In Alkaloids: Chemical and Biological Perspectives; Pelletier, S. W., Ed.; Springer-Verlag, New York, 1992.

[9]. Szantay, C.; Blasko, G.; Honty, K.; Dornyei, G. The Alkaloids; Brossi, A., Ed., Academic Press, Orlando, 1986.

[10]. Woodward, R. B.; Bader, F. E.; Bickel, H.; Frey, A. J.; Kierstead, R. W. J. Am. Chem. Soc. 1956, 78, 2023-2025.
http://dx.doi.org/10.1021/ja01590a079

[11]. Woodward, R. B.; Bader, F. E.; Bickel, H.; Kierstead, R. W. Tetrahedron 1958, 2, 1-57.
http://dx.doi.org/10.1016/0040-4020(58)88022-9

[12]. Pearlman, B. A. J. Am. Chem. Soc. 1979, 101, 6404-6408.
http://dx.doi.org/10.1021/ja00515a040

[13]. Wender, P. A.; Schaus, J. M.; White, A. W. J. Am. Chem. Soc. 1980, 102, 6157-6159.
http://dx.doi.org/10.1021/ja00539a038

[14]. Wender, P. A.; Schaus, J. M.; White, A. W. Hetereocycles 1987, 25, 263-270.
http://dx.doi.org/10.3987/S-1987-01-0263

[15]. Martin, S. F.; Grzejszczak, S.; Rueger, H.; Williamson, S. A. J. Am. Chem. Soc. 1985, 107, 4072-4072.
http://dx.doi.org/10.1021/ja00299a050

[16]. Martin, S. F.; Rueger, H.; Williamson, S. A.; Grzejszczak, S. J. Am. Chem. Soc. 1987, 109, 6124-6136.
http://dx.doi.org/10.1021/ja00254a036

[17]. Stork, G. Pure Appl. Chem. 1989, 61, 439-442.
http://dx.doi.org/10.1351/pac198961030439

[18]. Hanessian, S.; Pan, J. W.; Carnell, A.; Bouchard, H.; Lesage, L. J. Org. Chem. 1997, 62, 465-473.
http://dx.doi.org/10.1021/jo961713w
PMid:11671435

[19]. Chen, F.; Huang, J. Chem. Rev. 2005, 105, 4671-4706.
http://dx.doi.org/10.1021/cr050521a
PMid:16351058

[20]. Woodward, R. B. In Perspectives in Organic Syntheses, Todd, A. R., Ed., Interscience, New York, 1956.

[21]. Wender, P. A.; Schaus, J. M.; Torney, D. C. Tetrahedron Lett. 1979, 20, 2485-2488.
http://dx.doi.org/10.1016/S0040-4039(01)86327-9

[22]. Naito, T.; Hirata, Y.; Miyata, O.; Ninomiya, I.; Inoue, M.; Kamiichi, K.; Doi, M. Chem. Pharm. Bull. 1989, 37, 901-906.
http://dx.doi.org/10.1248/cpb.37.901

[23]. Miyata, O.; Hirata, Y.; Naito, T.; Ninomiya, I. Heterocycles 1984, 22, 1041-1044.
http://dx.doi.org/10.3987/R-1984-05-1041

[24]. Hochstein, F. A.; Paradies, A. M. J. Am. Chem. Soc. 1957, 79, 5735-5736.
http://dx.doi.org/10.1021/ja01578a041

Most read articles by the same author(s)
TrendMD

Dimensions - Altmetric - scite_ - PlumX

Downloads and views

Downloads

Download data is not yet available.

Metrics

Metrics Loading ...
License Terms

License Terms

by-nc

Copyright © 2024 by Authors. This work is published and licensed by Atlanta Publishing House LLC, Atlanta, GA, USA. The full terms of this license are available at https://www.eurjchem.com/index.php/eurjchem/terms and incorporate the Creative Commons Attribution-Non Commercial (CC BY NC) (International, v4.0) License (http://creativecommons.org/licenses/by-nc/4.0). By accessing the work, you hereby accept the Terms. This is an open access article distributed under the terms and conditions of the CC BY NC License, which permits unrestricted non-commercial use, distribution, and reproduction in any medium, provided the original work is properly cited without any further permission from Atlanta Publishing House LLC (European Journal of Chemistry). No use, distribution, or reproduction is permitted which does not comply with these terms. Permissions for commercial use of this work beyond the scope of the License (https://www.eurjchem.com/index.php/eurjchem/terms) are administered by Atlanta Publishing House LLC (European Journal of Chemistry).