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

11 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

All Science Journal Classification (ASJC) codes

  • Chemistry(all)

Fingerprint Dive into the research topics of 'Indium-catalyzed synthesis of keto esters from cyclic 1,3-diketones and alcohols and application to the synthesis of seratrodast'. Together they form a unique fingerprint.

  • Cite this