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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TL;DR: In this paper, an effective route to novel maleimides is described, which involves the reaction of an enamine derived from the addition of a secondary amine to a dialkyl acetylenedicarboxylate with an arylsulfonyl isocyanate.
53 citations
TL;DR: The density functional theory (DFT) study revealed that the strong σ-donating nature of the N-heterocyclic carbene ligand results in a strong C(carbene)-Au(III) interaction in the 1c-4c complexes.
Abstract: A series of gold(III) N-heterocyclic carbene complexes [1-(R1)-3-(R2)imidazol-2-ylidene]AuBr3 [R1 = i-Pr, R2 = CH2Ph (1c); R1 = mesityl, R2 = CH2Ph (2c); R1 = i-Pr, R2 = CH2COt-Bu (3c), and R1 = t-...
52 citations
TL;DR: Three approaches for stereoselective syntheses of cyclic enaminones and their functionalized derivatives are summarized: chiral substrates (chirons) as starting materials, syntheses employing non-catalytic (stoichiometric) reagents, and catalytic asymmetric methods.
51 citations
TL;DR: The four-component coupling-amination-aza-annulation-Pictet-Spengler (CAAPS) sequence of acid chlorides 1, terminal alkynes 2, tryptamine derivatives 6, and acryloyl chloride derivatives 4 represents a facile and rapid one-pot access to tetrahydro-beta-carbolines 7 in moderate to good yields.
51 citations
TL;DR: In this article, the Eschenmoser episulfide contraction was used for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-1.
Abstract: Practical total syntheses of the natural products fuligocandin A (2a) and fuligocandin B (3) have been achieved through a convergent strategy depending on the Eschenmoser episulfide contraction as a key step. Conducting the reaction in DMSO proved to be an efficient and general method for the synthesis of a variety of vinylogous amides, such as azepan-2-ylidenepropan-2-one.
42 citations
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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
40 citations