Asymmetric Friedel - Crafts Reaction: An Application to the Synthesis of an Etodolac Analogue
- 1 October 1996
- journal article
- research article
- Published by Taylor & Francis in Synthetic Communications
- Vol. 26 (19) , 3671-3676
- https://doi.org/10.1080/00397919608003781
Abstract
An Etodolac analogue, (-)-7, was prepared in 40% ee. by asymmetric Friedel-Crafts reaction, involving tryptophol 4 and chiral β-ketobutyrate 5f, followed by hydrolysis.Keywords
This publication has 11 references indexed in Scilit:
- Will the real β-pinene please stand upMagnetic Resonance in Chemistry, 1994
- Asymmetric steering of the Pictet-Spengler reaction by means of amino acid esters as chiral auxiliary groupsTetrahedron, 1994
- Synthesis of optically active 4-hydroxymandelic acid and derivatives via Regio- and Stereoselective Friedel-Crafts alkylation.Tetrahedron: Asymmetry, 1993
- New chiral auxiliaries derived from β -pinene: Their use in the asymmetric reduction of β-keto-estersTetrahedron: Asymmetry, 1991
- Enantioselective construction of dialkylcarbinols: synthesis of (-)-5-hexadecanolideJournal of the American Chemical Society, 1987
- Camphor derivatives as chiral auxiliaries in asymmetric synthesisTetrahedron, 1987
- Enantioselective synthesis of .beta.-amino esters through high pressure-induced addition of amines to .alpha.,.beta.-ethylenic estersJournal of the American Chemical Society, 1986
- Resolution of etodolac and antiinflammatory and prostaglandin synthetase inhibiting properties of the enantiomersJournal of Medicinal Chemistry, 1983
- Etodolic acid and related compounds. Chemistry and antiinflammatory actions of some potent di- and trisubstituted 1,3,4,9-tetrahydropyrano[3,4-b]indole-1-acetic acidsJournal of Medicinal Chemistry, 1976
- Preparation of an optically active prostaglandin intermediate via asymmetric inductionJournal of the American Chemical Society, 1975