| Title | An attempt to construct the C/D ring system of parkacine by intramolecular cycloaddition of azomethine ylide and alkyne |
| Authors | Zhang, Wenxuan Wang, Jiming Luo, Xihuan Meng, Xiangbao Li, Zhongjun |
| Affiliation | Peking Univ, State Key Lab Nat & Biomimet Drugs, Dept Biol Chem, Sch Pharmaceut Sci, Beijing 100191, Peoples R China. |
| Keywords | Lycorine-type alkaloids Parkacine Intramolecular cycloaddition Azomethine ylide Imine-enamine tautomerism IMINE-ENAMINE TAUTOMERISM HUMAN LEUKEMIA-CELLS AMARYLLIDACEAE ALKALOIDS LYCORINE DERIVATIVES APOPTOSIS (+/-)-LYCORINE |
| Issue Date | 2016 |
| Publisher | TETRAHEDRON LETTERS |
| Citation | TETRAHEDRON LETTERS.2016,57,(18),1981-1984. |
| Abstract | Intramolecular 1,3-dipolar cycloaddition of chiral hept-6-yne-azomethine ylide was attempted to construct the CM ring system of a lycorine-type alkaloid parkacine (3). However, the cycloaddition reactions gave C/D ring-closure product with opposite configurations at 7- and 7a-carbons, comparing with the natural product. The unexpected epimerization of phenyl substituted chiral carbon may occur through imine-enamine tautomerism before the intramolecular cycloaddition. (C) 2016 Elsevier Ltd. All rights reserved. |
| URI | http://hdl.handle.net/20.500.11897/438197 |
| ISSN | 0040-4039 |
| DOI | 10.1016/j.tetlet.2016.03.076 |
| Indexed | SCI(E) |
| Appears in Collections: | 药学院 天然药物与仿生药物国家重点实验室 |
