24173-65-7Relevant academic research and scientific papers
SYNTHESES OF OPTICALLY ACTIVE (+)-FRAGROLIDE AND (+)-BEMADIENOLIDE FROM DEHYDROABIETIC ACID
Akita, Hiroyuki,Anazawa, Akira,Oishi, Takeshi
, p. 1588 - 1593 (2007/10/02)
14-Hydroxydehydroabietane derivatives (8 and 9), having an oxygen functional group at the 6-position, were obtained from 14-hydroxy-7-oxodehydroabietane (10) by transformation of the 7-oxo group into a 6-acetoxyl (or hydroxyl) group.Ozonolysis of the above phenols (8 and 9) and subsequent reduction gave the 6-oxygenated confertifolin derivatives 17 and 19, respectively.Oxidation of 6-hydroxyconfertifolin (19) afforded the optically active (+)-fragrolide (4).On the other hand, 19 was also converted into (+)-bemadienolide (5) by oxidation of the important intermediate, 6β-phenylselenoconfertifolin (25).Keywords: - aromatic ring cleavage; drimanic sesquiterpenes; phenolic diterpenes; ozonolysis; transfer of ketone
