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.
Published Version
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