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
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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
New syntheses of (±)-tashiromine and (±)-epitashiromine via enaminone intermediates.
TL;DR: The syntheses of the naturally occurring indolizidine alkaloid (±)-tashiromine and its unnatural epimer (±-epitashirOMine are demonstrated through the use of enaminone chemistry.
Journal ArticleDOI
Synthesis of α-aryl enaminones through reactions of β-aryl enones with benzyl azide
TL;DR: The first metal free practical alternative to the preparation of acyclic α-aryl enaminones from commercially available or easily prepared starting materials is presented in this article. But the synthesis involves domino 1,3-dipolar cycloaddition and 1,2-aryl migration.
Journal ArticleDOI
A facile one-pot synthesis of acyclic β-enamino ketones, an important class of versatile synthetic intermediates
TL;DR: In this paper, a one-pot sequential process consisting of nucleophilic substitution of the lithiated acetylides with Weinreb amides followed by a Michael reaction of the extruded N -methoxy-N -methylamine after quenching with saturated NH 4 Cl, provided β-enamino ketones in high yield and in a single geometrical isomeric form.
Dissertation
Innate C-H functionalization of cyclic enaminones
TL;DR: Georg et al. as mentioned in this paper presented a Ph.D. dissertation on Chemistry at the University of Minnesota with a focus on the application of chemistry in the field of bio-medical imaging.
Journal ArticleDOI
π-Annulation reactions of 4-thiazolidinone enaminones in the synthesis of fused bi- and tri-cyclic compounds
TL;DR: The intramolecular vinylogous iminium ion 6-exo-trig cyclization was used to access fused bicyclic precursors for the π-annulation in order to obtain the novel tricyclic structures stereoselectively.
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.