Selective Lewis acid catalyzed transformation (gamma-butyrolactone versus cyclopropane) of 2-methoxy-4-benzyltetrahydrofuran derivatives. Efficient synthesis of lignan lactones.
[reaction: see text]. A short synthesis of lactone lignans exploiting a three-component coupling strategy is presented using a new Lewis acid catalyzed ring-opening/cyclization reaction of 2-methoxytetrahydrofuran derivatives 4 leading to gamma-butyrolactones as a key step. By simply changing the reaction conditions, it was possible, from the same substrates 4, to obtain selectively cyclopropane derivatives.
Ferrié
Laurent
L
Laboratoire de Chimie Organique 1, associé au CNRS, Université Claude Bernard Lyon 1, CPE, Villeurbanne, France.
Bouyssi
Didier
D
Balme
Geneviève
G
D015107:4-Butyrolactone / Q000737:chemistry*; D002384:Catalysis; D003500:Cyclization; D003521:Cyclopropanes / Q000138:chemical synthesis; D005663:Furans / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D017705:Lignans / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D003521:Cyclopropanes; D005663:Furans; D007783:Lactones; D017705:Lignans; C030797:cyclopropane; D015107:4-Butyrolactone