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Synthese von (±)-α-Chamigren. Vorläufige Mitteilung

✍ Scribed by György Fráter

Publisher
John Wiley and Sons
Year
1977
Tongue
German
Weight
155 KB
Volume
60
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthesis of (±)‐α‐Chamigrene

Cis‐ and trans‐β‐ionol (cis and trans‐1) underwent acid catalysed dehydration to a mixture of the tetraenes 2–5 in 70–80% yield (Table 1). Irradiation of this mixtures made the 6‐(Z), 8‐(Z)‐isomer 5 accessible (columns 3 and 4 in Table 1). Pyrolysis of the different mixtures at 170° showed, that both isomers, 3 and 5 respectively undergo electrocyclization to dehydrochamigrene (6). The latter was reduced to α‐chamigrene (7) by hydrogen on Lindlar catalyst.

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