European Journal of Chemistry 2012, 3(1), 26-31 | doi: https://doi.org/10.5155/eurjchem.3.1.26-31.503 | Get rights and content

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


Muhammad Yar (1,*) , Muhammad Arshad (2) , Muhammad Nadeem Akhtar (3) , Sohail Anjum Shahzad (4) , Islam Ullah Khan (5) , Zulfiqar Ali Khan (6) , Nisar Ullah (7) , Ichiya Ninomiya (8)

(1) Interdisciplinary Research Center in Biomedical Materials, Comsats Institute of Information Technology, Lahore, 54000, Pakistan
(2) Institute of Chemistry, University of the Punjab, Lahore, 54590, Pakistan
(3) Laboratory of Natural Products, Institute of Bioscience, University Putra Malaysia, Serdang, Selangor Darul Ehsan, 43400, Malaysia
(4) Department of Chemistry, Government College University, Lahore, 54000, Pakistan
(5) Department of Chemistry, Government College University, Lahore, 54000, Pakistan
(6) Department of Chemistry, Government College University, Faisalabad, 38000, Pakistan
(7) Department of Chemistry, King Fahd University of Petroleum and Minerals, Dhahran, 31261, Saudi Arabia
(8) International Center for Chemical and Biological Sciences, Hussain Ibrahim Jamal Research Institute of Chemistry, University of Karachi, Karachi, 75270, Pakistan
(*) Corresponding Author

Received: 19 Aug 2011 | Revised: 06 Oct 2011 | Accepted: 24 Oct 2011 | Published: 31 Mar 2012 | Issue Date: March 2012

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


Keywords


Lactam; Reserpine; Harmaline; Total synthesis; Enamide photocyclization; Hypertension and mental disorders

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DOI: 10.5155/eurjchem.3.1.26-31.503

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Higher Education Commission Pakistan, Pakistan

Citations

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[4]. Jisook Park, David Y.‐K. Chen
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How to cite


Yar, M.; Arshad, M.; Akhtar, M.; Shahzad, S.; Khan, I.; Khan, Z.; Ullah, N.; Ninomiya, I. Eur. J. Chem. 2012, 3(1), 26-31. doi:10.5155/eurjchem.3.1.26-31.503
Yar, M.; Arshad, M.; Akhtar, M.; Shahzad, S.; Khan, I.; Khan, Z.; 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(1), 26-31. doi:10.5155/eurjchem.3.1.26-31.503
Yar, M., Arshad, M., Akhtar, M., Shahzad, S., Khan, I., Khan, Z., Ullah, N., & Ninomiya, I. (2012). Studies towards the synthesis of (±)-reserpine: Photocyclization mediated a novel and efficient synthesis of 11,18-dimethoxy-(20α)-18,19-didehydro-yohimban-17-one. European Journal of Chemistry, 3(1), 26-31. doi:10.5155/eurjchem.3.1.26-31.503
Yar, Muhammad, Muhammad Arshad, Muhammad Nadeem Akhtar, Sohail Anjum Shahzad, Islam Ullah Khan, Zulfiqar Ali Khan, Nisar Ullah, & Ichiya Ninomiya. "Studies towards the synthesis of (±)-reserpine: Photocyclization mediated a novel and efficient synthesis of 11,18-dimethoxy-(20α)-18,19-didehydro-yohimban-17-one." European Journal of Chemistry [Online], 3.1 (2012): 26-31. Web. 8 Dec. 2021
Yar, Muhammad, Arshad, Muhammad, Akhtar, Muhammad, Shahzad, Sohail, Khan, Islam, Khan, Zulfiqar, Ullah, Nisar, AND Ninomiya, Ichiya. "Studies towards the synthesis of (±)-reserpine: Photocyclization mediated a novel and efficient synthesis of 11,18-dimethoxy-(20α)-18,19-didehydro-yohimban-17-one" European Journal of Chemistry [Online], Volume 3 Number 1 (31 March 2012)

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