https://pubs.rsc.org/en/content/articlepdf/2019/NP/C8NP00092A

Marine natural products.

The direct functionalization of C-H bonds in organic compounds has recently emerged as a powerful and ideal method for the formation of carbon-carbon and carbon-heteroatom bonds. This Review provides an overview of C-H bond functionalization strategies for the rapid synthesis of biologically active compounds such as natural products and pharmaceutical targets.

C-H bond functionalization: emerging synthetic tools for natural products and pharmaceuticals

In studying the evolution of organic chemistry and grasping its essence, one comes quickly to the conclusion that no other type of reaction plays as large a role in shaping this domain of science than carbon-carbon bond-forming reactions. The Grignard, Diels-Alder, and Wittig reactions are but three prominent examples of such processes, and are among those which have undeniably exercised decisive roles in the last century in the emergence of chemical synthesis as we know it today. In the last quarter of the 20th century, a new family of carbon-carbon bond-forming reactions based on transition-metal catalysts evolved as powerful tools in synthesis. Among them, the palladium-catalyzed cross-coupling reactions are the most prominent. In this Review, highlights of a number of selected syntheses are discussed. The examples chosen demonstrate the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.

Palladium-catalyzed cross-coupling reactions in total synthesis.

4.2.8. Reductive Coupling 3109 5. Reaction of Aromatic Compounds 3110 5.1. Electrophilic Substitutions 3110 5.2. Radical Substitution 3111 5.3. Oxidative Coupling 3111 5.4. Photochemical Reactions 3111 6. Reaction of Carbonyl Compounds 3111 6.1. Nucleophilic Additions 3111 6.1.1. Allylation 3111 6.1.2. Propargylation 3120 6.1.3. Benzylation 3121 6.1.4. Arylation/Vinylation 3121 6.1.5. Alkynylation 3121 6.1.6. Alkylation 3121 6.1.7. Reformatsky-Type Reaction 3122 6.1.8. Direct Aldol Reaction 3122 6.1.9. Mukaiyama Aldol Reaction 3124 6.1.10. Hydrogen Cyanide Addition 3125 6.2. Pinacol Coupling 3126 6.3. Wittig Reactions 3126 7. Reaction of R,â-Unsaturated Carbonyl Compounds 3127

Organic Reactions in Aqueous Media with a Focus on Carbon−Carbon Bond Formations: A Decade Update

The design and implementation of cascade reactions is a challenging facet of organic chemistry, yet one that can impart striking novelty, elegance, and efficiency to synthetic strategies. The application of cascade reactions to natural products synthesis represents a particularly demanding task, but the results can be both stunning and instructive. This Review highlights selected examples of cascade reactions in total synthesis, with particular emphasis on recent applications therein. The examples discussed herein illustrate the power of these processes in the construction of complex molecules and underscore their future potential in chemical synthesis.

Cascade reactions in total synthesis.

Synthesis of the tripeptide (C1–N12) and hydroxylated hexadecene (C26–C41) domains of sanglifehrin A and C

1(5)-Cyanosemibullvalene from barrelene. Spectral and crystal structure analysis of the marked equilibrium preference exerted by an efficient .pi.-electron acceptor substituent

Analysis of the first bands in the He(I) photoelectron spectra of “hypostrophene” (tetracyclo[5.3.0.02,6.03,10]deca-4,8-diene, 3), its tetrahydro- (1), dihydro- (2), homo- (4), and bishomo-derivative (5) has been achieved on the basis of the correlations within the series 1 to 5 with accompanying semiempirical calculations of the MINDO/3 and SPINDO/1 type. The electronic structure of the first excited states of 3 and syn-tricyclo[4.2.0.02,5]octadiene is discussed in light of their inability to undergo [π2s + π2s] ring closure.



Orbital-Wechselwirkungen in „Hypostrophen”, seinen Hydro- und Homo-Derivaten. Eine photoelektronenspektroskopische Untersuchung



Die Analyse der ersten Banden in den He(I)-Photoelektronen(PE)-Spektren von „Hypostrophen” (Tetracyclo[5.3.0.02,6.03,10]deca-4,8-dien, 3) sowie seiner Tetrahydro- (1), Dihydro- (2), Homo-(4) und Bishomo-Derivate (5) beruht auf der Korrelation zwischen den Spektren von 1 bis 5 sowie dem Vergleich mit den Ergebnissen von semiempirischen Rechnungen vom MINDO/3 und SPINDO/1-Typ. Die Elektronenstruktur des ersten angeregten Zustands von 3 und syn-Tricyclo[4.2.0.02,5]octadien wird im Zusammenhang mit dem Ausbleiben einer [π2s + π2s]- Reaktion diskutiert.

Orbital interactions in “hypostrophene” and its hydro-and homo-derivatives. A photoelectron spectroscopic investigation

Aus Cycloheptatrien (I) konnen die drei Homocycloheptatriene (II), (III) und (IV) gewonnen werden, von denen (III) weiter zu dem Homocycloheptatrien (V) umgesetzt werden kann.

Stereocontrolled synthesis, conformational features, and response to thermal activation of the seven possible bis- and trishomocycloheptatrienes

Synthesis, Chiroptical Properties, and Absolute Configuration of (+)-2,3-Dihydrotriquinacen-2-one. Effect of Rigid Triquinacene Geometry on the Inherently Dissymmetric Chromophore

Leo A. Paquette

Papers

Synthesis of the tripeptide (C1–N12) and hydroxylated hexadecene (C26–C41) domains of sanglifehrin A and C

1(5)-Cyanosemibullvalene from barrelene. Spectral and crystal structure analysis of the marked equilibrium preference exerted by an efficient .pi.-electron acceptor substituent

Orbital interactions in “hypostrophene” and its hydro-and homo-derivatives. A photoelectron spectroscopic investigation

Stereocontrolled synthesis, conformational features, and response to thermal activation of the seven possible bis- and trishomocycloheptatrienes

Synthesis, Chiroptical Properties, and Absolute Configuration of (+)-2,3-Dihydrotriquinacen-2-one. Effect of Rigid Triquinacene Geometry on the Inherently Dissymmetric Chromophore