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Synthese von (−)-(5R,6S)-5,6-Epoxy-5,6-dihydro-β-ionon

✍ Scribed by Murat Acemoglu; Walter Eschenmoser; Conrad Hans Eugster

Publisher
John Wiley and Sons
Year
1981
Tongue
German
Weight
296 KB
Volume
64
Category
Article
ISSN
0018-019X

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✦ Synopsis

Synthesis of (−)‐(5__R__,6__S__)‐5,6‐epoxy‐5,6‐dihydro‐β‐ionone

Optically active 5,6‐epoxy‐5,6‐dihydro‐β‐ionones have been prepared for the first time and their absolute configurations were determined by correlation with (−)‐(S)‐α‐ionone. Acid catalyzed hydrolysis of the epoxide proceeds with retention of the configuration at C(6) and with inversion at C(5).

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Diese erfreuliche Ubereinstimmung ist alles andere als trivial, wenn man bedenkt, wie viele verschiedene Argumente fur die Festlegung der absoluten Konfiguration der einzelnen Zwischenprodukte verwendet worden sind.