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.

Last updated on 2019-17-09 at 06:40