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Säurekatalysierte Umlagerung von 9-Hydroxyfuranoeremophilanen zu Eremophilanlactonen

✍ Scribed by Peter Siegenthaler; Markus Neuenschwander

Publisher
John Wiley and Sons
Year
1996
Tongue
German
Weight
877 KB
Volume
79
Category
Article
ISSN
0018-019X

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✦ Synopsis

Acid-Catalyzed Rearrangement of 9-Hydroxyfuranoeremophilanes to Eremophilanlactones 9-Hydroxyfuranoeremophilanes 1-3 are the main components of freshly harvested rhizomes of P. hybridus Ifuranopetasin chemovar, Table, Fig. I ) . They easily and quantitatively rearrange in the presence of traces of acid to give an epimeric mixture of 8-H-eremophilanlactones 4 4 (eremophilenolides, Table, Figs. and ) . Besides subsequent oxidation (see 4 + 7), this is the most important reaction occurring during drying and storage of rhizomes of P. hybridus (Figs. and ) . A reasonable mechanism of the rearrangement is presented, and spectroscopic structure elucidation of 8-H-eremophilanlactones is discussed.

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