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Issue 3, 2020
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Wagner–Meerwein type rearrangement in 5-oxohomoadamantane series

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Efficient methods for introducing various substituents into the α-position of ethyl 5-oxohomoadamantyl-4-carboxylate are reported. An unexpected acid-catalysed 1,2-alkyl shift in the series of synthesized α,α-bis-substituted 5-oxohomoadamantanes, and also in the hydroxy derivatives of homoadamantane was found. Such a retropinacol-like rearrangement leads to tetra- or pentacyclic mono- or bis-lactones containing a homoadamantane moiety. This new transformation opens access to the synthesis of previously unknown 2,4-di and 2,3,4-trisubstituted derivatives of homoadamantane. The resulting caged γ-butyro- and δ-valerolactones could be considered as potential synthetic or metabolic precursors of conformationally restricted GABA and δ-aminovaleric acid analogues.

Graphical abstract: Wagner–Meerwein type rearrangement in 5-oxohomoadamantane series

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Article information

20 Sep 2019
04 Dec 2019
First published
17 Dec 2019

Org. Biomol. Chem., 2020,18, 465-478
Article type

Wagner–Meerwein type rearrangement in 5-oxohomoadamantane series

I. M. Tkachenko, P. A. Mankova, V. B. Rybakov, E. V. Golovin and Y. N. Klimochkin, Org. Biomol. Chem., 2020, 18, 465
DOI: 10.1039/C9OB02060H

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