A short synthetic route to nordihydroguaiaretic acid (NDGA) and its stereoisomer using Ti-induced carbonyl-coupling reaction

✍ Scribed by Mikail H Gezginci; Barbara N Timmermann

• Book ID: 104231239
• Publisher: Elsevier Science
• Year: 2001
• Tongue: French
• Weight: 69 KB
• Volume: 42
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(01)01182-0

✦ Synopsis

A rapid synthetic approach to natural meso-nordihydroguaiaretic acid (NDGA) and its non-meso isomer is described from (3,4-dimethoxyphenyl)acetone using as a key step the low-valent Ti-induced carbonyl-coupling reaction of the ketone. The method involves a simple separation of the E-and Z-isomers that result from the dehydroxylation of the diol product of the coupling. The present approach allows the preparation of various analogs of NDGA.