Enantioselective Syntheses of Aeruginosin 298-A and Its Analogues Using a Catalytic Asymmetric Phase-Transfer Reaction and Epoxidation
- 22 August 2003
- journal article
- Published by American Chemical Society (ACS) in Journal of the American Chemical Society
- Vol. 125 (37), 11206-11207
- https://doi.org/10.1021/ja037290e
Abstract
We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogues, in which all stereocenters were controlled by a catalytic asymmetric phase-transfer reaction and epoxidation. Furthermore, drastic counteranion effects in phase-transfer catalysis were observed for the first time, making it possible to three-dimensionally fine-tune the catalyst (ketal part, aromatic part, and counteranion).This publication has 11 references indexed in Scilit:
- Enantioselective Amino Acid Synthesis by Chiral Phase-Transfer CatalysisChemical Reviews, 2003
- Development of new asymmetric two-center catalysts in phase-transfer reactionsTetrahedron Letters, 2002
- Catalytic Asymmetric Epoxidation of α,β-Unsaturated Amides: Efficient Synthesis of β-Aryl α-Hydroxy Amides Using a One-Pot Tandem Catalytic Asymmetric Epoxidation−Pd-Catalyzed Epoxide Opening ProcessJournal of the American Chemical Society, 2002
- First Total Syntheses of Aeruginosin 298-A and Aeruginosin 298-B, Based on a Stereocontrolled Route to the New Amino Acid 6-Hydroxyoctahydroindole-2-carboxylic AcidChemistry – A European Journal, 2001
- Total Synthesis and Reassignment of Configuration of Aeruginosin 298-AJournal of the American Chemical Society, 2000
- Molecular Design of a C2-Symmetric Chiral Phase-Transfer Catalyst for Practical Asymmetric Synthesis of α-Amino AcidsJournal of the American Chemical Society, 1999
- Remarkable ligand effect on the enantioselectivity of the chiral lanthanum complex-catalyzed asymmetric epoxidation of enonesTetrahedron Letters, 1998
- Aeruginosins 102-A and B, new thrombin inhibitors from the cyanobacterium Microcystis viridis (NIES-102)Tetrahedron, 1996
- Aeruginosin 298-A, a thrombin and trypsin inhibitor from the blue-green alga Microcystis aeruginosa (NIES-298)Tetrahedron Letters, 1994
- The stereoselective synthesis of .alpha.-amino acids by phase-transfer catalysisJournal of the American Chemical Society, 1989