Synthesis of the [8] gingerol enantiomers

✍ Scribed by Michel Martin; Philippe Guibet

• Publisher: John Wiley and Sons
• Year: 1991
• Tongue: English
• Weight: 436 KB
• Volume: 3
• Category: Article
• ISSN: 0899-0042
• DOI: 10.1002/chir.530030213

✦ Synopsis

• )-~S~-5-Hydroxy-l-~4-hydroxy-3-methoxyphenyl~-3-dodecanone l a commonly named ( + )-(S)-[81 gingerol is a natural product known to have cardiotonic activity.'-5 A total synthesis of both enantiomers is described with details for the first time using a general synthetic scheme which was recently outlined in the literature.6 This synthesis relies both on the separation of the diastereoisomers 4a and 4b by simple column chromatography on silica gel and on an HPLC analysis on a chiral phase to determine the optical purity of the enantiomers 8a and 8b of protected [81 gingerol. The gingerol isomers were thus obtained in good chemical yields in greater than 96% enantiomeric excess.