Eating five servings of fruits and vegetables per day! This is what is highly recommended and heavily advertised nowadays to the general public to stay fit and healthy! Drinking green tea on a regular basis, eating chocolate from time to time, as well as savoring a couple of glasses of red wine per day have been claimed to increase life expectancy even further! Why? The answer is in fact still under scientific scrutiny, but a particular class of compounds naturally occurring in fruits and vegetables is considered to be crucial for the expression of such human health benefits: the polyphenols! What are these plant products really? What are their physicochemical properties? How do they express their biological activity? Are they really valuable for disease prevention? Can they be used to develop new pharmaceutical drugs? What recent progress has been made toward their preparation by organic synthesis? This Review gives answers from a chemical perspective, summarizes the state of the art, and highlights the most significant advances in the field of polyphenol research.

Plant Polyphenols: Chemical Properties, Biological Activities, and Synthesis

Palladium-catalyzed carbonylation reactions of aromatic halides in the presence of various nucleophiles have undergone rapid development since the pioneering work of Heck and co-workers in 1974, such that nowadays a plethora of palladium catalysts are available for different carbonylative transformations. The carboxylic acid derivatives, aldehydes, and ketones prepared in this way are important intermediates in the manufacture of dyes, pharmaceuticals, agrochemicals, and other industrial products. In this Review, the recent academic developments in this area and the first industrial processes are summarized.

Palladium-catalyzed carbonylation reactions of aryl halides and related compounds.

C-C, C-O, C-N bond formation on sp2 carbon by Pd(II)-catalyzed reactions involving oxidant agents.

Synthesis of Heterocycles via Palladium-Catalyzed Carbonylations

10. Patented Literature 2616 10.1. Esterification 2616 10.2. Ether Formation 2619 10.2.1. Etherification without Cyclization 2619 10.2.2. Etherification with Cyclization 2624 10.3. N-Alkylation 2625 10.4. Other Reactions 2627 11. Summary and Outlook 2628 12. Note Added in Proof 2628 13. Abbreviations Used in This Review 2629 14. Acknowledgments 2629 15. Supporting Information Available 2630 16. References 2630

Mitsunobu and Related Reactions: Advances and Applications

Anti-inflammatory sesquiterpenes from Curcuma zedoaria

Total Synthesis of (−)-Cassine

An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin

Catalytic generation and trapping of acylmetals containing ni and cu with enolates

A total synthesis of the natural products, solamin 1 and reticulatacin 2 is described. The monotetrahydrofuran moiety 12a of compounds 1 and 2 was constructed by an eight-step reaction sequence, starting from (–)-muricatacin 5, an acetogenin derivative. The γ-lactone moieties 26 and 27 of compounds 1 and 2 were prepared by a multi-stage procedure, starting from (S)-(–)-ethyl lactate. A palladium-catalysed cross coupling reaction of compound 12a with either compound 26 or compound 27 gave the products 28 and 29 which by a three-step sequence were converted into compounds 1 and 2 respectively. Similarly, 15, 16-di-epi-solamin 3 and 17, 18-di-epi-reticulatacin 4 were synthesized.

Hidefumi Makabe

Papers

Anti-inflammatory sesquiterpenes from Curcuma zedoaria

Total Synthesis of (−)-Cassine

An efficient synthesis of procyanidins. Rare earth metal Lewis acid catalyzed equimolar condensation of catechin and epicatechin

Catalytic generation and trapping of acylmetals containing ni and cu with enolates

Total synthesis of solamin and reticulatacin