Säurekatalysierte Umlagerung von 7-Hydroxy-royleanon in ein 20(10→9) abeo-Abietan-Derivat und zwei Phenalenone
✍ Scribed by Marcel Hensch; Conrad Hans Eugster; Hans-Peter Weber
- Publisher
- John Wiley and Sons
- Year
- 1975
- Tongue
- German
- Weight
- 717 KB
- Volume
- 58
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Acid‐catalyzed rearrangement of 7‐hydroxyroyleanone into a 20(10→9) abeo‐abietane derivative and two phenalenones
Short treatment of either horminone (1b), taxoquinone (1a), 6,7‐dehydroroyleanone (3) or 6β‐hydroxyroyleanone (1c) with 80% H~2~SO~4~ at 0° leads to a mixture of rearranged products. Two of the structures, determined by X‐ray‐cristallography, were found to be (9__R__, 10__R__)‐20(10→9)‐abeo‐12‐hydroxy‐5,7, 12‐abietatriene‐11,14‐dione (4) and 9‐isopropyl‐2,2,5‐trimethyl‐8__H__‐phenaleno[1,9‐bc]furan‐8‐one (5), and the third compound, isolated in very small amounts, has been provisionally identified as 3‐hydroxy‐9‐isopropyl‐2,2,5‐trimethyl‐8__H__‐phenaleno[1,9‐bc]furan‐8‐one (6) from the spectroscopic data.