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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.
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European Journal of Chemistry
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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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[2]. Muhammad Yar, Lala Rukh Sidra, Eleni Pontiki, Nafeesa Mushtaq, Muhammad Ashraf, Rumana Nasar, Islam Ullah Khan, Nasir Mahmood, Syed Ali Raza Naqvi, Zulfiqar Ali Khan, Sohail Anjum Shahzad
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[3]. Christopher C. Nawrat, Christopher J. Moody
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[4]. Jisook Park, David Y.‐K. Chen
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[5]. Liangliang Song, Guilong Tian, Yi He, Erik V. Van der Eycken
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[6]. Zulfiqar Ali Khan, Sohail Anjum Shahzad, Arooj Anjum, Adebayo Tajudeen Bale, Syed Ali Raza Naqvi
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DOI: 10.1080/00397911.2018.1434546
[7]. Liangliang Song, Guilong Tian, Erik V. Van der Eycken
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[8]. Slavka Hamulakova, Zuzana Kudlickova, Ladislav Janovec, Roman Mezencev, Zachery J Deckner, Yury O Chernoff, Jana Janockova, Veronika Ihnatova, Petr Bzonek, Nikola Novakova, Vendula Hepnarova, Martina Hrabinova, Daniel Jun, Jan Korabecny, Ondrej Soukup, Kamil Kuca
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[9]. Christopher C. Nawrat, Christopher J. Moody
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DOI Link: https://doi.org/10.5155/eurjchem.3.1.26-31.503
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