Synthesis of Fluorinated (±)-Phoracantholide and Related Compounds: Regioselective Access to a Novel Class of Monofluorinated Fatty Acid Derivatives

✍ Scribed by Sattler, Andreas ;Haufe, Günter

• Publisher: John Wiley and Sons
• Year: 1994
• Tongue: English
• Weight: 506 KB
• Volume: 1994
• Category: Article
• ISSN: 0947-3440
• DOI: 10.1002/jlac.199419940913

✦ Synopsis

Abstract

10‐Fluorodecan‐9‐olide (1a), a monofluorinated analogue of (±)‐phoracantholide, is synthesised in 20% overall yield by a five‐step sequence starting with 9‐decenoic acid (3a). 10‐Undecenoic acid (3b) is transformed in 28% overall yield into the next higher homologue, 11‐fluoroundecan‐10‐olide (1b). Their regioisomers, 9‐fluorodecan‐10‐olide (2a) and 10‐fluoroundecan‐11‐olide (2b), are obtained analogously in 20% or 29% yield. Key step of these syntheses is the regioselective opening of the epoxides of unsaturated fatty acid esters 5a and 5b.