Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation

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

doi:10.1021/ja037290e

Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation

J Am Chem Soc. 2003 Sep 17;125(37):11206-7. doi: 10.1021/ja037290e.

Authors

Takashi Ohshima¹, Vijay Gnanadesikan, Tomoyuki Shibuguchi, Yuhei Fukuta, Tetsuhiro Nemoto, Masakatsu Shibasaki

Affiliation

¹ Graduate School of Pharmaceutical Sciences, The University of Tokyo, Hongo, Bunkyo-ku, Tokyo 113-0033, Japan.

PMID: 16220936
DOI: 10.1021/ja037290e

Abstract

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).

Publication types

Research Support, Non-U.S. Gov't

MeSH terms

Catalysis
Epoxy Compounds / chemistry*
Leucine / analogs & derivatives*
Leucine / chemical synthesis
Leucine / chemistry
Molecular Structure

Substances

Epoxy Compounds
aeruginosin 298-A
Leucine