Formation of Tetrahydrofurano-, Aryltetralin, and Butyrolactone Norlignans through the Epoxidation of 9-Norlignans

Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry
Patrik A RunebergPatrik Eklund

Abstract

Epoxidation of the C=C double bond in unsaturated norlignans derived from hydroxymatairesinol was studied. The intermediate epoxides were formed in up to quantitative conversions and were readily further transformed into tetrahydrofuran, aryltetralin, and butyrolactone products-in diastereomeric mixtures-through ring-closing reactions and intramolecular couplings. For epoxidation, the classical Prilezhaev reaction, using stoichiometric amounts of meta-chloroperbenzoic acid (mCPBA), was used. As an alternative method, a catalytic system using dimeric molybdenum-complexes [MoO2L]2 with ONO- or ONS-tridentate Schiff base ligands and aqueous tert-butyl hydroperoxide (TBHP) as oxidant was used on the same substrates. Although the epoxidation was quantitative when using the Mo-catalysts, the higher temperatures led to more side-products and lower yields. Kinetic studies were also performed on the Mo-catalyzed reactions.

References

Dec 11, 2003·Journal of Agricultural and Food Chemistry·Stefan M WillförBjarne R Holmbom
Jun 21, 2005·Chemical Society Reviews·Eric RoseMélanie Quelquejeu-Ethève
Sep 1, 2005·Organic & Biomolecular Chemistry·Patrik C EklundRainer E Sjöholm
Oct 19, 2007·Critical Reviews in Clinical Laboratory Sciences·Herman Adlercreutz
Jan 13, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Patrik Eklund, Jan-Erik Raitanen
Jan 18, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Patrik A RunebergPatrik C Eklund
Mar 9, 2019·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Carmen Rodríguez-GarcíaJosé J Gaforio

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Methods Mentioned

BETA
Epoxidation
NMR
size exclusion chromatography
column chromatography

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