Synthesis of sterically hindered chiral 1,4-diols from different lignan-based backbones
A1 Journal article (refereed)
Internal Authors/Editors
Publication Details
List of Authors: Yury Brusentsev, Mikko M. Hänninen, Patrik Eklund
Publisher: Georg Thieme Verlag
Publication year: 2013
Journal: Synlett
Volume number: 24
Issue number: 18
Start page: 2423
End page: 2426
eISSN: 1437-2096
Abstract
Methods for synthetic modifications of the natural dibenzylbutyrolactone lignan hydroxymatairesinol into chiral 1,4-diols with different lignan-derived backbones have been developed. A stepwise procedure, involving alkylation and oxidn., was shown to be successful and several highly substituted 1,4-diols, e.g., I, were prepd. One substituted butyrolactone intermediate resisted alkylation and led to the formation unusually stable hemiketals (butyrolactols) II (R = β-Me, α-Me). The formation of stable hemiketals was investigated in detail, showing that different backbone structures influence the formation and reactivity of the hemiketals.