Journal ArticleDOI
Enaminones: versatile intermediates for natural product synthesis*
Joseph P. Michael,C. B. De Koning,David Gravestock,Gladys D. Hosken,Arthur S. Howard,C. M. Jungmann,Rui W. M. Krause,Andrew S. Parsons,Stephen C. Pelly,Trevor V. Stanbury +9 more
TLDR
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.read more
Citations
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Journal ArticleDOI
Base-Mediated Selective Synthesis of Diversely Substituted N-Heterocyclic Enamines and Enaminones by the Hydroamination of Alkynes
TL;DR: The developed methodology provides an easy and novel access for the synthesis of enaminones 10a-c and supports the formation of cis-isomer by preferential addition of o-haloarylalkynes followed by intramolecular C2 arylation in the copper-catalyzed tandem synthesis of indolo and pyrrolo[2,1-a]isoquinolines.
Journal ArticleDOI
Intramolecular Additions of Various π-Nucleophiles to Chemoselectively Activated Amides and Application to the Synthesis of (±)-Tashiromine
TL;DR: This paper describes the comprehensive study of intramolecular addition of silyl enol ethers, allylsilanes, and enamines to chemoselectively activated formamides, aliphatic amides, and lactams and demonstrates that the species in solution after the cyclization are iminium ions, highly encouraging for the development of bis-cyclization strategies.
Journal ArticleDOI
Recent developments in chemical reactivity of N,N-dimethylenamino ketones as synthons for various heterocycles
TL;DR: In this paper, the authors present recent progress in the utility of N,N-dimethyl enaminones as building blocks for a diverse range of acyclic, carbocyclic and five-and six-membered heterocyclics.
Journal ArticleDOI
Silver-catalysed hydroamination : synthesis of functionalised pyrroles.
TL;DR: In this article, it was shown that functionalised pyrroles can be efficiently prepared using a two-step sequence using n-BuLi and propargyl bromide.
Journal ArticleDOI
Synthesis of 6- and 7-membered cyclic enaminones: scope and mechanism.
TL;DR: Six- and seven-membered cyclic enaminones can be prepared using common, environmentally benign reagents allowing diversification and the incorporation of chirality, and a β-amino elimination side reaction was identified in a few labile substrates that led to either loss of stereochemical purity or degradation.
References
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BookDOI
Alkaloids : chemical and biological perspectives
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.
Book
Strategies and Tactics in Organic Synthesis
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.