Precursors to oak lactone: synthesis of gallate ester derivatives of 3-methyl-4-hydroxyoctanoic acid

✍ Scribed by Michael Raunkjær; D.Sejer Pedersen; Gordon M. Elsey; Mark A. Sefton; George K. Skouroumounis

• Book ID: 104231935
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 60 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01890-1

✦ Synopsis

3R,4R-and 3S,4S)-3-Methyl-4-(3%-O-methylgalloyloxy)octanoic acid (2b), the corresponding methyl ester (2c) and the straight galloyl derivative, (3R,4R-and 3S,4S)-3-methyl-4-galloyloxyoctanoic acid (2a) were synthesised from cis-oak lactone (1). Analysis by TLC and mass spectrometry established that the original assignment of structure (2c) to a methylated natural oak component was in error.