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Experiments on the Total Synthesis of Lysolipin I. Part I. On Configuration and Conformation of 5-Substituted 1,2,3,4,4a,9,10,10a-Ocathydrophenanthrene-4,9-diones

✍ Scribed by Rudolf O. Duthaler; Peter Mathies; Walter Petter; Christoph Heuberger; Veronica Scherrer

Publisher
John Wiley and Sons
Year
1984
Tongue
German
Weight
265 KB
Volume
67
Category
Article
ISSN
0018-019X

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✦ Synopsis

Abstract

The substituted 1,2,3,4,4a,9,10,10a‐octahydrophenanthrene‐4,9‐dione 2, synthesized from the cyclohexanone 8 and quinone 11 (Scheme 2), was found by X‐ray analysis adn ^1^H‐NMR studies to be the isomer with cis‐junction of the saturated rings. The cis‐fusion could also be determined from the ^1^H‐NMR data of the related compound 17 (Scheme 4), which was previously considered to be trans‐fused. In contrary to previous argumentations, the interaction of the C(4)‐carbonyl O‐atom of trans‐fused octahydrophenanthenes is more severe with a 5‐methoxy than with a 5‐methyl substituent.

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