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

Research output: Contribution to journalArticle

80 Citations (Scopus)

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).

Original languageEnglish
Pages (from-to)11206-11207
Number of pages2
JournalJournal of the American Chemical Society
Volume125
Issue number37
DOIs
Publication statusPublished - Sep 17 2003
Externally publishedYes

Fingerprint

Epoxidation
Catalysis
Catalysts
aeruginosin 298-A

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Cite this

Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation. / Ohshima, Takashi; Gnanadesikan, Vijay; Shibuguchi, Tomoyuki; Fukuta, Yuhei; Nemoto, Tetsuhiro; Shibasaki, Masakatsu.

In: Journal of the American Chemical Society, Vol. 125, No. 37, 17.09.2003, p. 11206-11207.

Research output: Contribution to journalArticle

Ohshima, Takashi ; Gnanadesikan, Vijay ; Shibuguchi, Tomoyuki ; Fukuta, Yuhei ; Nemoto, Tetsuhiro ; Shibasaki, Masakatsu. / Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation. In: Journal of the American Chemical Society. 2003 ; Vol. 125, No. 37. pp. 11206-11207.
@article{62ee2c20d60a46a3b2b40da6eff255cc,
title = "Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation",
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).",
author = "Takashi Ohshima and Vijay Gnanadesikan and Tomoyuki Shibuguchi and Yuhei Fukuta and Tetsuhiro Nemoto and Masakatsu Shibasaki",
year = "2003",
month = "9",
day = "17",
doi = "10.1021/ja037290e",
language = "English",
volume = "125",
pages = "11206--11207",
journal = "Journal of the American Chemical Society",
issn = "0002-7863",
publisher = "American Chemical Society",
number = "37",

}

TY - JOUR

T1 - Enantioselective syntheses of aeruginosin 298-A and its analogues using a catalytic asymmetric phase-transfer reaction and epoxidation

AU - Ohshima, Takashi

AU - Gnanadesikan, Vijay

AU - Shibuguchi, Tomoyuki

AU - Fukuta, Yuhei

AU - Nemoto, Tetsuhiro

AU - Shibasaki, Masakatsu

PY - 2003/9/17

Y1 - 2003/9/17

N2 - 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).

AB - 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).

UR - http://www.scopus.com/inward/record.url?scp=0043194288&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0043194288&partnerID=8YFLogxK

U2 - 10.1021/ja037290e

DO - 10.1021/ja037290e

M3 - Article

C2 - 16220936

AN - SCOPUS:0043194288

VL - 125

SP - 11206

EP - 11207

JO - Journal of the American Chemical Society

JF - Journal of the American Chemical Society

SN - 0002-7863

IS - 37

ER -