New synthetic route to (S)-(−)-equol through allylic substitution

✍ Scribed by Yuji Takashima; Yuichi Kobayashi

• Book ID: 104095554
• Publisher: Elsevier Science
• Year: 2008
• Tongue: French
• Weight: 179 KB
• Volume: 49
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2008.06.085

✦ Synopsis

Allylic substitution of allylic picolinate 5 with a copper reagent derived from p-MeOC 6 H 4 MgBr (6) and CuBrÁMe 2 S produced the anti S N 2 0 product 7 with high regioselectivity and efficient chirality transfer. Oxidative cleavage of the olefinic function to the alcohol followed by bromination afforded bromide 16, which upon demethylation and intramolecular ether ring formation furnished (S)-(À)-equol (3).