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Säurekatalysierte Umlagerung von 7‐Hydroxy‐royleanon in ein 20(10→9) abeo ‐Abietan‐Derivat und zwei Phenalenone
Author(s) -
Hensch Marcel,
Eugster Conrad Hans,
Weber HansPeter
Publication year - 1975
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19750580708
Subject(s) - chemistry , furan , isopropyl , derivative (finance) , stereochemistry , medicinal chemistry , organic chemistry , financial economics , economics
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.