Chemie und Stereochemie der Iridoide, XIX. Zwei einfache EPC-Synthesen mit chemischem Beweis der absoluten Konfiguration von (+)-Mitsugashiwa-Lacton aus (S)-(−)-Citronellol und Aucubin
✍ Scribed by Weinges, Klaus ;Ziegler, Hans Jürgen ;Maurer, Wolfgang ;Schmidbauer, Stefan B.
- Publisher
- John Wiley and Sons
- Year
- 1993
- Tongue
- English
- Weight
- 353 KB
- Volume
- 1993
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Chemistry and Stereochemistry of Iridoids, XIX. – Two Straightforward EPC Syntheses with Chemical Evidence of Absolute Configuration of (+)‐Mitsugashiwa Lactone from (S)‐(−)‐Citronellol and Aucubin
Enantiomerically pure (+)‐Mitsugashiwa lactone (9) was prepared in eight steps from (S)‐(−)‐citronellol (1), whereas only four steps were required for the conversion of hexaacetylaucubin (10) into 9. Both starting materials are readily available in large quantities. The synthesis of 9 from 1 establishes the absolute configuration at C‐7 in 9. Conversely, the synthesis of 9 from 10 confirms the absolute configuration at C‐4a and C‐7a in 9.