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
No coin nor oath required. For personal study only.
✦ 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
📜 SIMILAR VOLUMES
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‐
See [14a]. BF,.Et,O-Catalyzed benzyloxylation of 3 led to partially racemized 4 (cu. 70%) [14b]. For other recent bcnzyloxylations of ~,P-unsaturated carbonyl compounds, see [14c].