A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction |
| |
| Authors: | Gaspar Diaz-Muñoz Raquel Geralda Isidorio Izabel Luzia Miranda Gabriel Nunes de Souza Dias Marisa Alves Nogueira Diaz |
| |
| Affiliation: | 1. Department of Chemistry, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil;2. Aquaculture-Veterinay School, Universidade Federal de Minas Gerais, Belo Horizonte, Minas Gerais 31270-901, Brazil;3. Department of Biochemistry and Molecular Biology, Universidade Federal de Viçosa, Minas Gerais 36570-900, Brazil |
| |
| Abstract: | The present study describes the total synthesis of 1,2,3,4-tetrahydroquinoline alkaloids (±)-galipinine, (±)-cuspareine, (±)-galipeine and (±)-angustureine, in three steps and high yields (78%, 76%, 74%, and 66%, respectively) from common aldehyde and the ylide respectives. The key step of this approach is based on an unusual Wittig reaction by using the phase transfer medium (aq. NaOH/CH2Cl2 1:1 or t-BuOK/t-BuOH/CH2Cl2 1:1), affording olefinic intermediates in high yields. |
| |
| Keywords: | Wittig reaction Phase transfer medium Tetrahydroquinoline alkaloids Corresponding author. |
| 本文献已被 ScienceDirect 等数据库收录！ |
|
