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

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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 2011-10-24
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.

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(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.

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