Enantioselective total synthesis of (S)-(−)-quinolactacin B |
| |
Authors: | Nagula Shankaraiah Carlos Kleber Z. Andrade |
| |
Affiliation: | a Laboratory of Asymmetric Synthesis, Chemistry Institute of Natural Resources, Universidad de Talca, Talca, PO Box 747, Talca, Region 7, Chile b Institute of Chemistry, Universidade de Brasília, UnB, Brasília, Brazil |
| |
Abstract: | The enantioselective total synthesis of (−)-quinolactacin B (−)-1 was performed in seven steps and 33% overall yield from tryptamine. The synthesis features the use of ruthenium catalytic asymmetric hydrogen reaction to introduce the chirality in dihydro-β-carboline 2. Based on Noyori’s work, the hydrogenation using the (R,R)-TsDPEN-Ru complex produces dihydro-β-carbolines possessing the (S) absolute configuration, the corrected asymmetric center of the natural product. The synthetic quinolactacin B displayed optical rotations that was in accordance with that of the natural product, thereby supporting the (S) configuration for natural quinolactacin B. The final product’s stereochemical assignment is in agreement with that proposed by Nakagawa and co-workers. |
| |
Keywords: | Quinolactacin B Noyori asymmetric hydrogenation Enantioselective Anodic oxidation |
本文献已被 ScienceDirect 等数据库收录! |
|