ol035617a_si_001.pdf (208.61 kB)
A Flexible Approach to (S)-5-Alkyl Tetramic Acid Derivatives: Application to the Asymmetric Synthesis of (+)-Preussin and Protected (3S,4S)-AHPPA
journal contribution
posted on 2003-11-13, 00:00 authored by Pei-Qiang Huang, Tian-Jun Wu, Yuan-Ping RuanA flexible asymmetric approach to 5-alkyl tetramic acid derivatives is described, which is based on the use of 9 as the first synthetic equivalent
to chiral nonracemic tetramic acid 5-carbanionic synthon 9b. The existence of the carbanion intermediate 9b was proven by trapping with
trimethylchlorosilane. Application of the present method to the synthesis of antifungal alkaloid (+)-preussin, as well as protected (3S,4S)-AHPPA 6, is also described.