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Enantioselective Syntheses of Aeruginosin 298-A and Its Analogues Using a Catalytic Asymmetric Phase-Transfer Reaction and Epoxidation

2003; American Chemical Society; Volume: 125; Issue: 37 Linguagem: Inglês

10.1021/ja037290e

1943-2984

Takashi Ohshima, Vijay Gnanadesikan, Tomoyuki Shibuguchi, Yuhei Fukuta, Tetsuhiro Nemoto, Masakatsu Shibasaki,

Asymmetric Synthesis and Catalysis

We developed a versatile synthetic process for aeruginosin 298-A as well as several attractive analogues, in which all stereocenters were controlled by a catalytic asymmetric phase-transfer reaction and epoxidation. Furthermore, drastic counteranion effects in phase-transfer catalysis were observed for the first time, making it possible to three-dimensionally fine-tune the catalyst (ketal part, aromatic part, and counteranion).