Total Synthesis of (−)-Cinatrin C1 Based on an In(OTf)3‑Catalyzed Conia-Ene Reaction

The stereocontrolled total synthesis of (−)-cinatrin C1, a phospholipase A2 inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)3-catalyzed Conia–ene reaction of the oxygen-tethered acetylenic malonic es...

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Published inJournal of organic chemistry Vol. 78; no. 8; pp. 3847 - 3857
Main Authors Urabe, Fumiya, Nagashima, Shunsuke, Takahashi, Keisuke, Ishihara, Jun, Hatakeyama, Susumi
Format Journal Article
LanguageEnglish
Published United States American Chemical Society 19.04.2013
Subjects
Catalysis
Lactones - chemical synthesis
Lactones - chemistry
Mesylates - chemistry
Molecular Structure
Stereoisomerism
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Summary:The stereocontrolled total synthesis of (−)-cinatrin C1, a phospholipase A2 inhibitor, has been accomplished. The key feature includes the stereoselective construction of the highly substituted tetrahydrofuran core by In(OTf)3-catalyzed Conia–ene reaction of the oxygen-tethered acetylenic malonic ester followed by dihydroxylation with concomitant lactonization.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
DOI:10.1021/jo400263w