Enamines: recent advances in synthetic, spectroscopic, mechanistic, and stereochemical aspects—I

13C NMR spectral analysis of lignans from Araucaria angustifolia

Intramolecular radical cyclization of suitably substituted epoxy ethers 4a−g using bis(cyclopentadienyl)titanium(III) chloride as the radical source resulted in trisubstituted tetrahydrofurano lignans and 2,6-diaryl-3,7-dioxabicyclo[3.3.0]octane lignans depending on the reaction conditions. The titanium(III) species was prepared in situ from commercially available titanocene dichloride and activated zinc dust in THF. Upon radical cyclization followed by acidic workup, epoxy olefinic ethers 4a−g afforded furano lignans dihydrosesamin 1a, lariciresinol dimethyl ether 1b, acuminatin methyl ether 1e, and sanshodiol methyl ether 1g directly and lariciresinol 1h, acuminatin 1i, and lariciresinol monomethyl ether 1j after removal of the benzyl protecting group by controlled hydrogenolysis of the corresponding cyclized products. The furofuran lignans sesamin 2a, eudesmin 2b, and piperitol methyl ether 2e were also prepared directly by using the same precursors 4a−f on radical cyclization followed by treatment wit...

Short and stereoselective total synthesis of furano lignans (+/-)-dihydrosesamin, (+/-)-lariciresinol dimethyl ether, (+/-)-acuminatin methyl ether, (+/-)-sanshodiol methyl ether, (+/-)-lariciresinol, (+/-)-acuminatin, and (+/-)-lariciresinol monomethyl ether and furofuran lignans (+/-)-sesamin, (+/-)-eudesmin, (+/-)-piperitol methyl ether, (+/-)-pinoresinol, (+/-)-piperitol, and (+/-)-pinoresinol monomethyl ether by radical cyclization of epoxides using a transition-metal radical source.

The distribution of lignanoids in the order coniferae

Phenolic and terpenoid heartwood constituents of Libocedrus yateensis

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The Chemistry of the Order Cupressales. 56. Heartwood Constituents of Fitzroya cupressoides (Monlina) Johnston.

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Fiber Surface Modification. Part III. The Reaction of Lignin Model Compounds and Other Phenols with Cyanuric Chloride.

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Phosphorus Spin-Lattice Relaxation in Phophorus Trioxide.

/pdf/quantitative-analysis-of-polyethylene-glycol-monododecyl-3esyc96119.pdf

Quantitative Analysis of Polyethylene Glycol Monododecyl Ethers by Gas Chromatography after Silylation.

/pdf/n-quaternary-compounds-part-iv-stereoselective-sulphoxide-13ndvw2kce.pdf

T. Mattila

Papers

The Chemistry of the Order Cupressales. 56. Heartwood Constituents of Fitzroya cupressoides (Monlina) Johnston.

Fiber Surface Modification. Part III. The Reaction of Lignin Model Compounds and Other Phenols with Cyanuric Chloride.

Phosphorus Spin-Lattice Relaxation in Phophorus Trioxide.

Quantitative Analysis of Polyethylene Glycol Monododecyl Ethers by Gas Chromatography after Silylation.

N-Quaternary Compounds. Part IV. Stereoselective Sulphoxide Formation.