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Journal ArticleDOI

Enaminones: versatile intermediates for natural product synthesis*

30 Jun 1999-Pure and Applied Chemistry (International Union of Pure and Applied Chemistry)-Vol. 71, Iss: 6, pp 979-988
TL;DR: In this article, an overview of the chemistry of enaminones and related compounds containing the structural unit N-CaC-Z (Za COR, CO2R, CN, NO2, S O 2Ar, etc.).
Abstract: Efforts in our laboratories to devise a general approach to the synthesis of alkaloids focus on the versatile reactivity of enaminones and related compounds containing the structural unit N-CaC-Z (Za COR, CO2R, CN, NO2 ,S O 2Ar, etc.). This lecture presents an overview of our research with these useful building blocks. Themes to be elaborated include chemo- selectivity and diastereoselectivity in reactions of enaminones, and the challenge of controlling absolute stereochemistry.

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Citations
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Journal ArticleDOI
TL;DR: Enaminoketones and enaminonitriles have proven to be versatile building blocks for the synthesis of various heterocycles such as pyridine, pyrimidine and pyrrole derivatives.

165 citations

Journal ArticleDOI
TL;DR: A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide.
Abstract: A variety of β-enamino ketones and esters have been synthesized in high to exellent yields by reacting β-dicarbonyl compounds with amines in the presence of a catalytic amount of indium tribromide. The reaction proceeds smoothly at room temperature in a short reaction time under solvent-free conditions.

126 citations

Journal ArticleDOI
TL;DR: Bismuth(III) trifluoroacetate has been found to be an extremely efficient catalyst for the preparation of β-enaminones in water as discussed by the authors, and by employing this catalyst, high regio-and chemoselective enamination of carbonyl compounds was achieved.

110 citations

Journal ArticleDOI
TL;DR: Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.
Abstract: A new reaction for the preparation of enaminones has been discovered. This method employs β-amino acids as starting materials to allow diversification as well as incorporation of chirality. The β-amino acids, once converted to ynones, are readily cyclized to the desired six-membered enaminone via a two-step, one-pot protocol. Although disguised as a 6-endo-dig cyclization, the reagents employed in the transformation play a direct role in bond making and bond breaking, thus changing the mode of addition.

84 citations

Journal ArticleDOI
TL;DR: In this article, a zinc-mediated reformatsky reaction between diethyl bromomalonate and N -arylpyrrolidine-2-thiones was used to synthesize quinolone antibiotics.

82 citations

References
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BookDOI
01 Jan 1991
TL;DR: In this paper, the total synthesis of amaryllidaceae alkaloids has been studied using radical cyclization reactions in total syntheses of naturally occurring indole alkaloid.
Abstract: Chapter headings. Carbon-13 and proton NMR shift assignments and physical constants of diterpenoid alkaloids. Supercritical fluid extraction of alkaloids. Recent advances in the total synthesis of amaryllidaceae alkaloids. Applications of radical cyclization reactions in total syntheses of naturally occurring indole alkaloids.

1,263 citations

Book
29 Jun 1993
TL;DR: This paper presents the first total Synthesis of several Natural Products Based On Alkyne-Co2(Co2)6 Complexes, and discusses the design and synthesis of Cooperative "Pinwheel" Fluorescent Sensors, and the application of Silicon-Ass Intramolecular Cross-Coupling.
Abstract: Chapter 1. The Total Synthesis Of Luzopeptins. Chapter 2. Synthesis of Geldanamycin Using Glycolate Aldol Reactions. Chapter 3. From Methylene Bridged Glycoluril Dimers To Cucurbit[N]Uril Analogs With Some Detours Along The Way. Chapter 4. Application Of Silicon-Assisted Intramolecular Cross-Coupling In Total Synthesis Of (+)-Brasilenyne. Chapter 5. Samarium(II) Promoted Ketyl Olefin Cyclizations Applied To The Total Syntheses Of (-)-Steganone And (+)-Isoschizandrin. Chapter 6. The Synthesis Of Polycavernoside A. An Example Of Conformationally Guided Macrolactonization. Chapter 7. First Total Synthesis Of Several Natural Products Based On Alkyne-Co2(Co)6 Complexes. Chapter 8. Total Synthesis Of Myriaporones 1, 3, and 4. Chapter 9. Adventures In Natural Product Synthesis: From Deep Sea Sponge To Pilot Plant. The Large Scale Total Synthesis Of The Marine Natural Product (+)-Discodermolide. Chapter 10. Synthesis Of Aprepitant. Chapter 11. Total Synthesis And Mechanism Of Action Studies On The Antitumor Alkaloid,(-)-Agelastatin A. Chapter 12. Design And Synthesis of Cooperative "Pinwheel" Fluorescent Sensors. Chapter 13. Functionalization Of Pyridines And Thiazoles Via The Halogen-Dance Reaction, Application To The Total Synthesis Of Caerulomycin C And WS75624 B. Chapter 14. Diastereoselective Intramolecular 4+3 Cycloaddition And An Enantioselective Total Synthesis Of (+)-Dactylol.

175 citations