Synthesis of sterically hindered chiral 1,​4-​diols from different lignan-​based backbones

A1 Originalartikel i en vetenskaplig tidskrift (referentgranskad)


Interna författare/redaktörer


Publikationens författare: Yury Brusentsev, Mikko M. Hänninen, Patrik Eklund
Förläggare: Georg Thieme Verlag
Publiceringsår: 2013
Tidskrift: Synlett
Volym: 24
Nummer: 18
Artikelns första sida, sidnummer: 2423
Artikelns sista sida, sidnummer: 2426
eISSN: 1437-2096


Abstrakt

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.

Senast uppdaterad 2019-16-10 vid 03:24