Concise total synthesis of (-)-protoemetinol
Journal of Pharmaceutical Care & Health Systems

Journal of Pharmaceutical Care & Health Systems
Open Access

ISSN: 2376-0419

Concise total synthesis of (-)-protoemetinol

6th Asia-Pacific Pharma Congress

July 11-13, 2016 Kuala Lumpur, Malaysia

Changjin Lim, Hyunyoung Moon, Kyeojin Kim, Jaehoon Sim, Seyeon Hwang, Hongchan An, Seung-Mann Paek and Young-Ger Suh

Seoul National University, Republic of Korea
Gyeongsang National University, Republic of Korea

Posters & Accepted Abstracts: J Pharma Care Health Sys

Abstract :

Benzo[?±]quinolizidine alkaloids have received constant attention because of their multiple pharmacological interests. Particularly, emetine, which acts as a protein synthesis inhibitor and DNA interacting agent has been clinically used for the treatment of a protozoan infection. Recently, additional biological activities, including antiviral properties and NF-?ºB signaling inhibitory effects, were reported. Tubulosine also exhibits various biological activities such as broad cytotoxicity in cancer cell lines, antimalarial activity, HIV reverse transcriptase-inhibitory activity and HIF-1 transcriptional inhibitory activity. (-)-Protoemetinol could be an excellent intermediate for the synthesis of various benzo[?±]quinolizidine alkaloids including emetine and tubulosine because the structure of protoemetinol is identical to that of the core upper part of those alkaloids. The stereoselective synthesis of (-)-protoemetinol has been accomplished through nine steps from a known homoallylic amine. The key steps of the synthesis involve the efficient preparation of an aza-Claisen rearrangement (ACR) precursor using cross metathesis and amide enolate-induced ACR followed by acid-catalyzed transannulation for the elaboration of the benzo[a]quinolizine skeleton and three stereogenic centers. This unique synthetic route envisages a unified and versatile strategy for the synthesis of 2,3-disubstituted benzo[a]quinolizidine.

Biography :

Changjin Lim has received his Bachelor’s degree in Pharmacy from Seoul National University in 2011. He is currently a PhD candidate in the laboratory of Professor Young-Ger Suh at Seoul National University, South Korea.

Email: [email protected]