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Proof of the Absolute Configuration of (−)‐( S )‐2‐Hydroxy‐β‐ionone by correlation with ursolic acid and with (−)‐ trans ‐verbenol
Author(s) -
Escher Sina,
Giersch Wolfgang,
Ohloff Günther
Publication year - 1981
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.19810640402
Subject(s) - chemistry , ionone , ursolic acid , absolute configuration , stereochemistry , terpene , triterpene , two dimensional nuclear magnetic resonance spectroscopy , medicine , alternative medicine , pathology , chromatography
(−)‐( S )‐2‐Hydroxy‐β‐ionone ( 33 ), (+)‐(2 S , 6 S )‐2‐hydroxy‐α‐ionone ( 34 ), and their acetates 35 and 36 have been synthesized from (+)‐( S )‐6‐methylbicyclo [4.3.0]‐non‐1‐ene‐3, 7‐dione ( 3 ). The key intermediate (+)‐(1 R , 3 S , 6 S )‐2, 2, 6‐trimethyl‐7‐oxobicyclo [4.3.0]non‐3‐yl acetate ( 7 ) was correlated with a degradation product of the pentacyclic triterpene ursolic acid ( 16 ). Compound 33 was also synthesized by an alternative route starting from (−)‐ trans ‐verbenol ( 42 ).