Jump to main content
Jump to site search


Wagner–Meerwein type rearrangement in 5-oxohomoadamantane series

Author affiliations

Abstract

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

Back to tab navigation

Supplementary files

Article information


Submitted
20 Sep 2019
Accepted
04 Dec 2019
First published
17 Dec 2019

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

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, Advance Article , DOI: 10.1039/C9OB02060H

Social activity

Search articles by author

Spotlight

Advertisements