Synthesis of prostaglandins by conjugate addition and alkylation of a directed enolate ion. 4,5-Allenyl prostaglandins

• Published in: Journal of organic chemistry Vol. 55; no. 20; pp. 5528 - 5531
• Main Author: Patterson, John W
• Format: Journal Article
• Language: English
• Published: Washington, DC American Chemical Society 01.09.1990
• Subjects: 551000 - Physiological Systems; ACETIC ACID; ADSORBENTS; ALCOHOLS; Alicyclic compounds, terpenoids, prostaglandins, steroids; ALKALI METAL COMPOUNDS; ALKENES; ALKYLATION; ANIONS; BASIC BIOLOGICAL SCIENCES; BROMIDES; BROMINE COMPOUNDS; CARBANIONS; CARBOXYLIC ACIDS; CHARGED PARTICLES; CHEMICAL PREPARATION; CHEMICAL REACTIONS; Chemistry; CHROMATOGRAPHY; COPPER COMPOUNDS; COPPER HALIDES; COPPER IODIDES; DECOMPOSITION; ENOLS; ETHERS; Exact sciences and technology; HALIDES; HALOGEN COMPOUNDS; HYDROCARBONS; HYDROLYSIS; HYDROXY COMPOUNDS; INFRARED SPECTRA; IODIDES; IODINE COMPOUNDS; IONS; ISOMERS; LIQUID COLUMN CHROMATOGRAPHY; LITHIUM BROMIDES; LITHIUM COMPOUNDS; LITHIUM HALIDES; LYSIS; MONOCARBOXYLIC ACIDS; NMR SPECTRA; ORGANIC ACIDS; Organic chemistry; ORGANIC COMPOUNDS; ORGANIC OXYGEN COMPOUNDS; ORGANIC SILICON COMPOUNDS; OXIDATION; Preparations and properties; PROSTAGLANDINS; RACEMATES; SEPARATION PROCESSES; SILICA GEL; SOLVOLYSIS; SPECTRA; SYNTHESIS; THIN-LAYER CHROMATOGRAPHY; TRANSITION ELEMENT COMPOUNDS; Prostaglandin; Aliphatic compound; Epimer; Ketol; Secondary alcohol; Allenic compound; Allylic compound; Monocyclic compound

Over the previous two decades many elegant syntheses of prostaglandins, which in more sophisticated forms, allow the stereospecific introduction of the various asymmetric carbons have been accomplished. However, among these approaches the cuprate addition/enolate alkylation of suitable cyclopentenon...