Recent developments in natural product synthesis using metal-catalysed C–H bond functionalisation

Chemical Society Reviews, Год журнала: 2011, Номер 40(4), С. 1885 - 1885

Опубликована: Янв. 1, 2011

Metal-catalysed C–H bond functionalisation has had a significant impact on how chemists make molecules. Translating the methodological developments to their use in assembly of complex natural products is an important challenge for continued advancement chemical synthesis. In this tutorial review, we describe selected recent examples metal-catalysed been able positively affect synthesis products.

Язык: Английский

---

The medicinal chemist's toolbox for late stage functionalization of drug-like molecules

Chemical Society Reviews, Год журнала: 2015, Номер 45(3), С. 546 - 576

Опубликована: Окт. 28, 2015

The advent of modern C-H functionalization chemistries has enabled medicinal chemists to consider a synthetic strategy, late stage (LSF), which utilizes the bonds drug leads as points diversification for generating new analogs. LSF approaches offer promise rapid exploration structure activity relationships (SAR), generation oxidized metabolites, blocking metabolic hot spots and preparation biological probes. This review details toolbox intermolecular with proven applicability drug-like molecules, classified by regioselectivity patterns, gives guidance on how systematically develop strategies using these patterns other considerations. In addition, number examples illustrate have been used impact actual discovery chemical biology efforts.

Язык: Английский

---

Transition metal-catalyzed C–H bond functionalizations by the use of diverse directing groups

Organic Chemistry Frontiers, Год журнала: 2015, Номер 2(9), С. 1107 - 1295

Опубликована: Янв. 1, 2015

In this review, a summary of transition metal-catalyzed C–H activation by utilizing the functionalities as directing groups is presented.

Язык: Английский

---

Rhodium Catalyzed Chelation-Assisted C–H Bond Functionalization Reactions

Accounts of Chemical Research, Год журнала: 2011, Номер 45(6), С. 814 - 825

Опубликована: Дек. 8, 2011

Over the last several decades, researchers have achieved remarkable progress in field of organometallic chemistry. The development metal-catalyzed cross-coupling reactions represents a paradigm shift chemical synthesis, and today synthetic chemists can readily access carbon–carbon carbon–heteroatom bonds from vast array starting compounds. Although we cannot understate importance these methods, required prefunctionalization to carry out adds cost reduces availability reagents.The use C–H bond activation lieu has presented tantalizing alternative classical reactions. Researchers met challenges selectivity reactivity associated with functionalization an explosion creative advances substrate catalyst design. Literature reports on based steric effects, acidity, electronic directing group effects are now numerous.Our developed that take advantage chelating group, this Account surveys our area. chelation control offers advantages respect scope application total synthesis. predictability decreased dependence inherent stereoelectronics generally result selective high yielding transformations broad applicability. nature moiety be chosen serve as functional handle subsequent elaborations.Our work began Rh(I) catalysts intramolecular aromatic annulations, which further include enantioselective transformations. chemistry simple olefinic found α,β-unsaturated imines allowed highly substituted olefins, pyridines, piperidines. We observed complementary Rh(III) oxidative coupling unactivated alkenes. Further studies led us develop methods for polarized π such those isocyanates. In cases chelation-controlled been applied synthesis complex molecules natural products, highlighting utility organic

Язык: Английский

---

C–H functionalization logic in total synthesis

Chemical Society Reviews, Год журнала: 2011, Номер 40(4), С. 1976 - 1976

Опубликована: Янв. 1, 2011

In this critical review, the strategic and economic benefits of C-H functionalization logic will be analyzed through lens total synthesis. order to illustrate dramatically simplifying effects type can potentially have on synthetic planning, we take reader a series case studies in which it has already been successfully applied. first section, chronological look at key historical syntheses examined, leading into modern day examples. second our own experience with applying executing synthesis "mindset" discussed (114 references).

Язык: Английский

---