Sammanfattning
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.
Originalspråk | Odefinierat/okänt |
---|---|
Sidor (från-till) | 2423–2426 |
Tidskrift | Synlett |
Volym | 24 |
Nummer | 18 |
DOI | |
Status | Publicerad - 2013 |
MoE-publikationstyp | A1 Tidskriftsartikel-refererad |