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Synthesis of doubly labeled enantiomerically pure (R)-mevalonolactone from lactic and malic acid

✍ Scribed by Krohn, Karsten ;Meyer, Annegrete


Book ID
102901947
Publisher
John Wiley and Sons
Year
1994
Tongue
English
Weight
896 KB
Volume
1994
Category
Article
ISSN
0947-3440

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✦ Synopsis


Abstract

Enantiomerically pure ^13^C‐ and ^1^H‐labeled (R)‐mevalonolactones are prepared from (S)‐malic and/or (S)‐lactic acid by Seebachs methodology of self‐reproduction of chirality. The two reaction pathways are complementary in the possibilities of multiple isotopic labeling. The labeling potential is exemplified by the synthesis of a doubly ^13^C, ^1^H‐labeled, one ^13^C‐, and one ^1^H‐labeled mevalonolactone. magnified image


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✍ Jean-Claude Barrière; Jeanine Cléophax; Stephan D. Géro; Marc Vuilhorgne 📂 Article 📅 1983 🏛 John Wiley and Sons 🌐 German ⚖ 698 KB

The synthesis of a large variety of enantiomerically pure substituted reactive cyclopentenes **16, 23, 24** and **28** have been synthesized from the readily available (−)‐quinic acid **1**. The straightforward strategy involves a high‐yielding intramolecular aldolization‐dehydration of acyclic 1,6‐