A Unified Stereodivergent Strategy for Prostaglandin and Isoprostanoid Synthesis

Acetoxyfulvene surrended to asymmetric Diels–Alder cycloaddition, paving the way to the development of a unified strategy for the stereodivergent synthesis of both prostaglandins and isoprostanoids. In fact, the cycloadduct was subsequently converted to a common intermediate, which through two diffe...

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Published inJournal of organic chemistry Vol. 79; no. 6; pp. 2632 - 2639
Main Authors Valli, Matteo, Chiesa, Francesco, Gandini, Andrea, Porta, Alessio, Vidari, Giovanni, Zanoni, Giuseppe
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 21.03.2014
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
Cycloaddition Reaction
Lactones - chemistry
Molecular Structure
Physical Sciences
Prostaglandins - chemical synthesis
Prostaglandins - chemistry
Science & Technology
Stereoisomerism
PATHWAYS
DIELS-ALDER REACTIONS
ACETOXYFULVENE SYNTHESIS
COMPLEXES
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Summary:Acetoxyfulvene surrended to asymmetric Diels–Alder cycloaddition, paving the way to the development of a unified strategy for the stereodivergent synthesis of both prostaglandins and isoprostanoids. In fact, the cycloadduct was subsequently converted to a common intermediate, which through two different stereoselective pathways afforded the two lactones 1 and 2, which are key building blocks in the synthesis of prostaglandins and isoprostanoids, respectively.
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ISSN:0022-3263
1520-6904
DOI:10.1021/jo500093k