Enantioselective synthesis of (S)-trans-γ-butenynyl γ-aminobutyric acid (GABA)
- 1 January 1991
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 12,p. 3307-3313
- https://doi.org/10.1039/p19910003307
Abstract
The enantioselective synthesis of (S)-trans-g;-butenynyl γ-aminobutyric acid (GABA)1 by phthalimide displacement of the (R)-alcohol 9(generated from the acetal 3) is reported. Novel hydride reductions of the pentadiynylic ether 3 to the trans-enyne 5 are reported and discussed.Keywords
This publication has 19 references indexed in Scilit:
- Enantioselective synthesis of (S)-γ-acetylenic γ-aminobutyric acid (GABA) and (S)-trans-γ-butenynyl GABAJournal of the Chemical Society, Chemical Communications, 1989
- A novel route to allenyl fluorides. Synthesis of 4-amino-7-fluorohepta-5,6-dienoic acid, the first fluoroallenyl amino acidJournal of the American Chemical Society, 1987
- Allylamine Derivatives—a New Class of Active Substances in Antifungal ChemotherapyAngewandte Chemie International Edition in English, 1987
- 1,4-BIS(TRIMETHYLSILYL)BUTA-1,3-DIYNEOrganic Syntheses, 1987
- Allenic amino acids. 1. Synthesis of .gamma.-allenic GABA by a novel aza-Cope rearrangementJournal of the American Chemical Society, 1984
- The cis of 4-(trimethylsilyl)-3-butyn-2-ol with lithium aluminium hydrideTetrahedron Letters, 1983
- Asymmetric synthesis via acetal templates. 4. Reactions with silylacetylenic compounds. Formation of chiral propargylic alcoholsJournal of the American Chemical Society, 1983
- Inhibitors of GABA metabolismBiochemical Pharmacology, 1979
- A Novel Carbon-Carbon Bond Scission and the Isomerization Mechanism of Vinylaluminum CompoundsJournal of the American Chemical Society, 1963
- Dialkylaluminiumhydride als sterisch spezifische Reduktionsmittel für AcetyleneEuropean Journal of Inorganic Chemistry, 1956