121st General Meeting of the KCS

Type Poster Presentation
Area Organic Chemistry
Room No. Event Hall
Time 4월 19일 (목요일) 11:00~12:30
Code ORGN.P-539
Subject Asymmetric synthesis of piperidine alkaloids microcosamine A and microgrewiapine A from chiral azirines
Authors Lingamurthy Macha, Hyun-Joon Ha1,*
Chemistry, Hankuk University of Foreign Studies, Korea
1Department of Chemistry, Hankuk University of Foreign Studies, Korea
Abstract 2-Methyl-3-hydroxy-6-alkylated piperidines constitute an important class of natural alkaloids with their interesting biological and pharmacological properties (anaesthetic, analgesic, antitumor, antibiotic, CNS stimulating biological properties, antihypertensive and antifungal activities etc.). A divergent, new, and highly stereoselective synthesis of 2-methyl-3-hydroxy-6-alkylated piperidine natural products including microgrewiapine, microcosamine has been accomplished from aziridine-2(S)- carboxylate as chiral pool starting material. Key features of the strategy include the utility of N-methylative aziridine ring opening reaction, intramolecular reductive amination reaction to form the piperidine framework in high yields and Julia–Kocienski olefination to install the triene side-chain. References: 1. For selected reviews of piperidine alkaloids, see:(a) H. Makabe, Stud. Nat. Prod. Chem., 2014, 42, 353–371; (b) I. Ojima and D. M. Iula, Alkaloids: Chemical and Biological Perspectives, Elsevier, Oxford, UK, 1999, vol. 13, p. 371–412. 2. Representative references, for isolation, see: (a) P. C. Still, B. Yi, T. F. G. Cestari, L. Pan, R. E. Pavlovicz, H. B. Chai, T. N. Ninh, C. Li, D. D. Soejarto, D. B. McKay and A. D. Kinghorn, J. Nat. Prod., 2013, 76, 243–249. (b) C. Viegas Jr., V. da S. Bolzani, M. Furlan, E. J. Barreiro, M. C. M. Young, D. Tomazela and M. N. Eberlin, J. Nat. Prod., 2004, 67, 908–910. 3. C. Rajireddy, B. Latha, K. Warudikar, K.K. Singarapu, Org. Biomol. Chem., 2016, 14, 251–258.
E-mail mlmurthy4u@gmail.com