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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: This brief review discusses the application of cyclic enaminones as building blocks, as well as potential intermediates in the total synthesis of selected alkaloids.

71 citations

Journal ArticleDOI
TL;DR: In this article, the performance of different supported heteropoly acids (HPAs) in the synthesis of β-enaminones and βenamino esters from various substituted amines and β-diketones or β-keto esters has been studied.

70 citations

Journal ArticleDOI
TL;DR: Silica supported perchloric acid (HClO 4 ·SiO 2 ) has been utilized as a heterogeneous recyclable catalyst for a highly efficient and chemo- and stereoselective conversion of β-dicarbonyl compounds by treatment with amines at room temperature into β-enaminones and β-ENamino esters under solvent-free conditions as discussed by the authors.
Abstract: Silica supported perchloric acid (HClO 4 ·SiO 2 ) has been utilized as a heterogeneous recyclable catalyst for a highly efficient and chemo- and stereoselective conversion of β-dicarbonyl compounds by treatment with amines at room temperature into β-enaminones and β-enamino esters under solvent-free conditions.

67 citations

Book ChapterDOI
01 Jan 2010
TL;DR: In this paper, the coupling-isomerization reaction (CIR) was used for the synthesis of 3-halo furans, pyrroles, pyrazoles and annelated pyridines.
Abstract: Alkynones and chalcones are of paramount importance in heterocyclic chemistry as three-carbon building blocks. In a very efficient manner, they can be easily generated by palladium-copper catalyzed reactions: ynones are formed from acid chlorides and terminal alkynes, and chalcones are synthesized in the sense of a coupling-isomerization (CI) sequence from (hetero)aryl halides and propargyl alcohols. Mild reaction conditions now open entries to sequential and consecutive transformations to heterocycles, such as furans, 3-halo furans, pyrroles, pyrazoles, substituted and annelated pyridines, annelated thiopyranones, pyridimines, meridianins, benzoheteroazepines and tetrahydro-β-carbolines, by consecutive coupling-cyclocondensation or CI-cyclocondensation sequences, as new diversity oriented routes to heterocycles. Domino reactions based upon the coupling-isomerization reaction (CIR) have been probed in the synthesis of antiparasital 2-substituted quinoline derivatives and highly luminescent spiro-benzofuranones and spiro-indolones.

66 citations

Journal ArticleDOI
TL;DR: In this article, alkyl azides were reacted with enones in the presence of Lewis acids to give enaminones (vinylogous amides), which formally involve a ring contraction reaction.

65 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