Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast

Yoichiro Kuninobu, Atsushi Kawata, Taihei Noborio, Syun Ichi Yamamoto, Takashi Matsuki, Kazumi Takata, Kazuhiko Takai

Research output: Contribution to journalArticle

9 Citations (Scopus)

Abstract

Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.

Original languageEnglish
Pages (from-to)941-945
Number of pages5
JournalChemistry - An Asian Journal
Volume5
Issue number4
DOIs
Publication statusPublished - Apr 1 2010
Externally publishedYes

Fingerprint

seratrodast
Indium
Esters
Alcohols
Carbon
Anti-Asthmatic Agents
Lewis Acids
Eicosanoids
Esterification
Silver
Functional groups
Catalyst activity
Iron
trifluoromethanesulfonic acid

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Cite this

Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast. / Kuninobu, Yoichiro; Kawata, Atsushi; Noborio, Taihei; Yamamoto, Syun Ichi; Matsuki, Takashi; Takata, Kazumi; Takai, Kazuhiko.

In: Chemistry - An Asian Journal, Vol. 5, No. 4, 01.04.2010, p. 941-945.

Research output: Contribution to journalArticle

Kuninobu, Yoichiro ; Kawata, Atsushi ; Noborio, Taihei ; Yamamoto, Syun Ichi ; Matsuki, Takashi ; Takata, Kazumi ; Takai, Kazuhiko. / Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast. In: Chemistry - An Asian Journal. 2010 ; Vol. 5, No. 4. pp. 941-945.
@article{0c5c2f61debe44239604c9fe8e73b66d,
title = "Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast",
abstract = "Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.",
author = "Yoichiro Kuninobu and Atsushi Kawata and Taihei Noborio and Yamamoto, {Syun Ichi} and Takashi Matsuki and Kazumi Takata and Kazuhiko Takai",
year = "2010",
month = "4",
day = "1",
doi = "10.1002/asia.200900553",
language = "English",
volume = "5",
pages = "941--945",
journal = "Chemistry - An Asian Journal",
issn = "1861-4728",
publisher = "John Wiley and Sons Ltd",
number = "4",

}

TY - JOUR

T1 - Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast

AU - Kuninobu, Yoichiro

AU - Kawata, Atsushi

AU - Noborio, Taihei

AU - Yamamoto, Syun Ichi

AU - Matsuki, Takashi

AU - Takata, Kazumi

AU - Takai, Kazuhiko

PY - 2010/4/1

Y1 - 2010/4/1

N2 - Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.

AB - Esterification reactions from cyclic 1,3-diketones and alcohols are carried out in the presence of several Lewis acids. In particular, indium(III) triflate, In(OTf)3, iron(III) triflate, Fe-(OTf)3, copper(II) triflate, Cu(OTf)2, and silver(I) triflate, AgOTf, show high catalytic activities. These reactions proceed through the carbon-carbon bond cleavage by a retro-aldol reaction and were found to be highly regioselective even in the presence of other functional groups. This type of reaction can also be applied to the preparation of the keto esters during the synthesis of seratrodast, which is an antiasthmatic and eicosanoid antagonist.

UR - http://www.scopus.com/inward/record.url?scp=77950846274&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=77950846274&partnerID=8YFLogxK

U2 - 10.1002/asia.200900553

DO - 10.1002/asia.200900553

M3 - Article

C2 - 20235270

AN - SCOPUS:77950846274

VL - 5

SP - 941

EP - 945

JO - Chemistry - An Asian Journal

JF - Chemistry - An Asian Journal

SN - 1861-4728

IS - 4

ER -