New synthetic route to (S)-(−)-equol through allylic substitution |
| |
| Authors: | Yuji Takashima |
| |
| Institution: | Department of Biomolecular Engineering, Tokyo Institute of Technology, Box B52, Nagatsuta-cho 4259, Midori-ku, Yokohama 226-8501, Japan |
| |
| Abstract: | Allylic substitution of allylic picolinate 5 with a copper reagent derived from p-MeOC6H4MgBr (6) and CuBr·Me2S produced the anti SN2′ 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)-(−)-equol (3). |
| |
| Keywords: | |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
