H. Amer, K. Mereiter, C. Stanetty, A. Hofinger, L. Czollner, I. Beseda, U. Jordis, B. Küenburg, D. Classen-Houben, P. Kosma:
"Synthesis and crystal structures of ring A modified glycyrrhetinic acid derivatives derived from 2,3-oxirane and 2,3-thiirane intermediates";
Tetrahedron, 66 (2010), S. 4390 - 4402.

Kurzfassung englisch:
A general method for the introduction of thiol groups at positions 1, 2, and 3 of glycyrrhetinic acid has
been developed starting from a protected 2a,3a-oxido-derivative. Conversion into the corresponding
2b,3b-epithio-derivative was followed by ring-opening leading to either 2- or 3-substituted thio derivatives.
Conversely, 3a-configured allylic alcohol intermediates derived from the 2,3-epoxide provided
efficient access to both diastereoisomeric 3-thio derivatives as well as 1a-thio derivatives. The stereochemistry
of the newly formed stereogenic centers was rigorously proven using X-ray crystallography.

Terpenoids, Glycyrrhetinic acid, Rearrangement, Thiirane, Oxirane

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