6.4. Polyynes 3123 6.5. Using R-Hydroxy Stannanes 3124 6.6. Using the Hurtley Reaction 3124 6.7. Using a Methylenation Reaction 3125 7. Conclusions and Future Prospects 3125 8. Uncommon Abbreviations 3125 9. Acknowledgments 3125 10. Note Added in Proof 3125 11. References 3126 * Authorstowhomcorrespondenceshouldbeaddressed(evano@chimie.uvsq.fr, nicolas.blanchard@uha.fr). † Université de Versailles Saint Quentin en Yvelines. ‡ Université de Haute-Alsace. Chem. Rev. 2008, 108, 3054–3131 3054

Copper-mediated coupling reactions and their applications in natural products and designed biomolecules synthesis.

Copper-catalyzed Ullmann condensations are key reactions for the formation of carbon-heteroatom and carbon-carbon bonds in organic synthesis. These reactions can lead to structural moieties that are prevalent in building blocks of active molecules in the life sciences and in many material precursors. An increasing number of publications have appeared concerning Ullmann-type intermolecular reactions for the coupling of aryl and vinyl halides with N, O, and C nucleophiles, and this Minireview highlights recent and major developments in this topic since 2004.

Catalytic C-C, C-N, and C-O Ullmann-type coupling reactions.

Spectrometric Identification of Organic Compounds

Natural and synthetic chromenes, fused chromenes, and versatility of dihydrobenzo[h]chromenes in organic synthesis.

The Complementary Competitors: Palladium and Copper in C-N Cross-Coupling Reactions

Ethnobotany, phytochemistry, and pharmacology of the genus Litsea: An update.

Ullmann reaction in tetraethyl orthosilicate: a novel synthesis of triarylamines and diaryl ethers

Two new monoterpenoid coumarins: anisucumarin A (1) and B (2), a pair of epimers, were isolated from Clausena anisum-olens. Their structures were established based on extensive spectroscopic analyses.

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New monoterpenoid coumarins from Clausena anisum-olens

A new coumarin, anisucoumaramide (1), and a new δ-truxinate derivative, anisumic acid (2), were isolated from Clausena anisum-olens. Their structures were elucidated from extensive NMR and MS data. The absolute configurations of the coumarins were assigned using the experimental and calculated electronic circular dichroism data. Anisucoumaramide (1) represents the first example of a naturally occurring coumarin of which the terpenoidal side chain does not comply with the biosynthesis isoprene rule due to the presence of an unprecedented acetamido motif directly connected with the terpenoidal side chain. The δ-truxinate derivative was isolated from Clausena species for the first time. Compound 1 showed high selectivity for the MAO-B isoenzyme and inhibitory activity in the nanomolar range. Putative biosynthesis pathways toward 1 and 2 are proposed.

Anisucoumaramide, a Bioactive Coumarin from Clausena anisum-olens

Chemical examination of the BuOH extract of the leaves and twigs of Litsea glutinosa collected from Xishuangbanna resulted in the isolation of two new aporphine alkaloids, namely litseglutine A (1) and B (2), along with two known aporphine alkaloids, boldine (3) and laurolitsine (4). The structures of the new alkaloids have been elucidated on the basis of spectra analysis as 6-demethyl-9-methoxy-1,2-(methylenedioxy)aporphin10-ol (=6,7,7a,8-tetrahydro-10-methoxy-5H-benzo[g]-1,3-benzodioxolo[6,5,4-de]quinolin-11-ol;1) and 1,10,11-trimethoxyaporphin-2-ol (=5,6,6a,7-tetrahydro-1,10,11-trimethoxy-6-methyl-4H-dibenzo[deg]quinolin-2-ol; 2).

Yun-Song Wang

Papers

Ethnobotany, phytochemistry, and pharmacology of the genus Litsea: An update.

Ullmann reaction in tetraethyl orthosilicate: a novel synthesis of triarylamines and diaryl ethers

New monoterpenoid coumarins from Clausena anisum-olens

Anisucoumaramide, a Bioactive Coumarin from Clausena anisum-olens

Two New Aporphine Alkaloids from Litsea glutinosa