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The Relative Stabilities of Substituted cis- and trans-1,2,3,4,4a,9,10,10a-Octahydrophenanthrenes, Including Configurational Corrections in the Elad-Ginsburg Morphine Synthesis

✍ Scribed by Rudolf O. Duthaler; David Ginsburg

Publisher
John Wiley and Sons
Year
1986
Tongue
German
Weight
481 KB
Volume
69
Category
Article
ISSN
0018-019X

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✦ Synopsis

The relative configuration of the title compounds has been determined by 'H-NMR measurements at 300 MHz. In contradistinction to prevailing opinion, it was found that 4-OXO derivatives prefer the cis-configuration. While the cis/truns ratio is 82: 18 for the parent 1,2,3,4,4a,9,10, lOa-octahydrophenanthrene-4,9-dione, the transisomers of C(5)-substituted derivatives cannot be detected under the conditions of equilibration. The cis-configuration is retained upon acetalization of the 4-ox0 derivative. A warning is issued regarding the assigned configurations of certain intermediates in the Elud-Ginsburg synthesis of morphine.

Schemc

I A:gfl 02CH3 _c H o ~c o Z c H 3

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Experiments on the Total Synthesis of Ly
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
✍ Rudolf O. Duthaler; Peter Mathies; Walter Petter; Christoph Heuberger; Veronica 📂 Article 📅 1984 🏛 John Wiley and Sons 🌐 German ⚖ 265 KB

## 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