Enantioselective total synthesis of (S)-(-)-quinolactacin B

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-beta-carboline 2. Based on Noyori's work, the hydrogenation using the (R,R)-TsDPEN-Ru complex produces dihydro-beta-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. (C) 2008 Elsevier Ltd. All rights reserved.