A concise and efficient synthesis of tetrahydroquinoline alkaloids using the phase transfer mediated Wittig olefination reaction

作者：Diaz Munoz Gaspar; Isidorio Raquel Geralda; Miranda Izabel Luzia; de Souza Dias Gabriel Nunes; Nogueira Diaz Marisa Alves

来源：Tetrahedron Letters, 2017, 58(33): 3311-3315.

DOI：10.1016/j.tetlet.2017.07.044

• Wittig reaction
• Phase transfer medium
• Tetrahydroquinoline alkaloids
• Galipea officinalis

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.

• 出版日期2017-8-16