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Author

Philip Magnus

Other affiliations: Indiana University
Bio: Philip Magnus is an academic researcher from University of Texas at Austin. The author has contributed to research in topics: Indole test & Ring (chemistry). The author has an hindex of 38, co-authored 224 publications receiving 3948 citations. Previous affiliations of Philip Magnus include Indiana University.


Papers
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Journal ArticleDOI
TL;DR: In this article, the triisopropylsilyl (TIPS) enol ethers were treated with PhIO/TMSN3/at −18 to −15 °C rapidly (5 min) with only traces of the α-azido adduct.
Abstract: Treatment of triisopropylsilyl (TIPS) enol ethers with PhIO/TMSN3/at −18 to −15 °C rapidly (5 min) gave β-azido TIPS enol ethers in high yields, with only traces of the α-azido adduct. The reaction...

133 citations

Journal ArticleDOI
TL;DR: This is the shortest synthesis of codeine (13 steps, 20% overall yield) and, for the first time, allows access to codeine without having to reduce codeinone.
Abstract: Suzuki coupling of 7 to 8 gave the biphenyl derivative 9. Reaction of 9 with ethyl vinyl ether/bromine/base gave 10, which on treatment with CsF/DMF at 130 °C resulted in the cross-conjugated 2,5-cyclohexadienone 6. Acid hydrolysis of 6 gave 11, which was reductively aminated to give (±)-narwedine 2. Since 2 has been converted into (−)-galanthamine 1 in two steps, this synthesis proceeds in eight steps with an overall yield of 63%. Also treatment of the cross-conjugated cyclohexadienone 6 with nitromethane/base gave 12, which was reduced to provide 13. Reduction of the nitro group in 13 to an amine, followed by reductive amination under acidic conditions, arrives at the codeine skeleton 15. Elaboration of 15 into (±)-codeine proceeds via the previously unknown α-epoxide derivative 18. This is the shortest synthesis of codeine (13 steps, 20% overall yield) and, for the first time, allows access to codeine without having to reduce codeinone.

115 citations

Journal ArticleDOI
TL;DR: Fissure coupling of the fluoranthene adduct (7,12-diphenyl)benzo[k]fluoranthene (3) using AlCl3/NaCl, CoF3/TFA, or Tl(OCOCF3) gave the new polyaromatic hydrocarbon dibenzo{[f,f]]-4,4’,7,7’-tetraphenyl}diindeno[1,2,3-cd:1‘,2
Abstract: Fissure coupling of the fluoranthene adduct (7,12-diphenyl)benzo[k]fluoranthene (3) using AlCl3/NaCl, CoF3/TFA, or Tl(OCOCF3) gave the new polyaromatic hydrocarbon dibenzo{[f,f’]-4,4’,7,7’-tetraphenyl}diindeno[1,2,3-cd:1‘,2‘,3‘-lm]perylene (4). Crystal data for 4: triclinic space group P1, a = 10.569(2) A, b = 11.565(4) A, c = 13.001(3) A, α = 95.05(2)°, β = 111.24(1)°, γ = 100.53(1)°, Z = 1, RF = 0.075%. Compounds 3 and 4 are both highly fluorescent in solution and display relative fluorescence quantum yields of φF = 1.0 and 0.85, respectively. The electrochemistry and electrogenerated chemiluminescence (ECL) of each compound has been investigated. The cyclic voltammogram of 3 in benzene−acetonitrile (9:1) shows that the compound undergoes a reversible reduction and an irreversible oxidation, whereas the cyclic voltammogram of 4 displays the reversible formation of both singly and doubly charged cations and anions. Compounds 3 and 4 undergo ECL to yield blue and orange-red light, respectively, with an ...

108 citations

Journal ArticleDOI
TL;DR: In this article, a variety of α,β-unsaturated ketones with Mn(dpm)3 (3 mol%)/PhSiH3 (1.3 equiv.)/isopropyl alcohol/O2, followed by reductive work-up with P(OEt)3 resulted in the formation of α-hydroxyketones.

99 citations


Cited by
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TL;DR: This review covers the literature published in 2014 for marine natural products, with 1116 citations referring to compounds isolated from marine microorganisms and phytoplankton, green, brown and red algae, sponges, cnidarians, bryozoans, molluscs, tunicates, echinoderms, mangroves and other intertidal plants and microorganisms.

4,649 citations

Journal ArticleDOI
TL;DR: MCRs and especially MCRs with isocyanides offer many opportunities to attain new reactions and basic structures, however, this requires that the chemist learns the "language" of M CRs, something that this review wishes to stimulate.
Abstract: Multicomponent reactions (MCRs) are fundamentally different from two-component reactions in several aspects. Among the MCRs, those with isocyanides have developed into popular organic-chemical reactions in the pharmaceutical industry for the preparation of compound libraries of low-molecular druglike compounds. With a small set of starting materials, very large libraries can be built up within a short time, which can then be used for research on medicinal substances. Due to the intensive research of the last few years, many new backbone types have become accessible. MCRs are also increasingly being employed in the total synthesis of natural products. MCRs and especially MCRs with isocyanides offer many opportunities to attain new reactions and basic structures. However, this requires that the chemist learns the “language” of MCRs, something that this review wishes to stimulate.

3,619 citations

Journal ArticleDOI
TL;DR: 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.
Abstract: 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.

2,391 citations

Journal ArticleDOI
TL;DR: In this Review, highlights of a number of selected syntheses are discussed, demonstrating the enormous power of these processes in the art of total synthesis and underscore their future potential in chemical synthesis.
Abstract: 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.

2,268 citations

Journal ArticleDOI
TL;DR: I. Foldamer Research 3910 A. Backbones Utilizing Bipyridine Segments 3944 1.
Abstract: III. Foldamer Research 3910 A. Overview 3910 B. Motivation 3910 C. Methods 3910 D. General Scope 3912 IV. Peptidomimetic Foldamers 3912 A. The R-Peptide Family 3913 1. Peptoids 3913 2. N,N-Linked Oligoureas 3914 3. Oligopyrrolinones 3915 4. Oxazolidin-2-ones 3916 5. Azatides and Azapeptides 3916 B. The â-Peptide Family 3917 1. â-Peptide Foldamers 3917 2. R-Aminoxy Acids 3937 3. Sulfur-Containing â-Peptide Analogues 3937 4. Hydrazino Peptides 3938 C. The γ-Peptide Family 3938 1. γ-Peptide Foldamers 3938 2. Other Members of the γ-Peptide Family 3941 D. The δ-Peptide Family 3941 1. Alkene-Based δ-Amino Acids 3941 2. Carbopeptoids 3941 V. Single-Stranded Abiotic Foldamers 3944 A. Overview 3944 B. Backbones Utilizing Bipyridine Segments 3944 1. Pyridine−Pyrimidines 3944 2. Pyridine−Pyrimidines with Hydrazal Linkers 3945

1,922 citations