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
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Analogues of amphibian alkaloids: total synthesis of (5R,8S,8aS)-(-)-8-methyl-5-pentyloctahydroindolizine (8-epi-indolizidine 209B) and [(1S,4R,9aS)-(-)-4-pentyloctahydro-2H-quinolizin-1-yl]methanol
TL;DR: The methodology reported in this article was successfully applied to the enantioselective synthesis of the title compounds and paves the way for the total synthesis of a range of cis-5,8-disubstituted indolizidines and cis-1,4- Disubst ituted quinolizin-1-yl, as well as the naturally occurring trans-disubsided alkaloids.
Journal ArticleDOI
Two versatile routes towards Cerpegin and analogues: applications of a one pot reaction to new analogues of Cerpegin
Didier Villemin,Nawel Cheikh,Liang Liao,Nathalie Bar,Jean-François Lohier,Jana Sopkova,Noureddine Choukchou-Braham,Bachir Mostefa-Kara +7 more
TL;DR: In this paper, a simple and efficient route to the natural alkaloid Cerpegin and new analogues is described, where methylfuranones are condensed with dimethylformamide diethylacetal (DMFDEA) to yield enaminolactone esters.
Journal ArticleDOI
Novel quinoline bearing sulfonamide derivatives and their cytotoxic activity against MCF7 cell line
TL;DR: The present work reports the synthesis of novel 5-Oxo-5,6,7,8-tetrahydroquinoline and 2,5-dioxo-3,4,5, 6, 7, 8-Tetrahytochemical derivatives containing enaminone system and bearing a sulfonamide moiety, designed in compliance with the general pharmacophoric requirements for carbonic anhydrase inhibiting anticancer drugs.
Journal ArticleDOI
Preparation and reductive transformations of vinylogous sulfonamides (β-sulfonyl enamines), and application to the synthesis of indolizidines
TL;DR: These beta-sulfonyl enamines are sufficiently nucleophilic for cyclisation with internal electrophiles to give sulfone-substituted indolizines, potentially useful scaffolds for alkaloid synthesis.
Journal ArticleDOI
Enaminone-Derived Pyrazoles with Antimicrobial Activity
TL;DR: A series of pyrazoles derived from the substituted enaminones were synthesized and were evaluated for antimicrobial activity and compound (P11) was found to have highest activity against both Gram-positive and Gram-negative bacteria.
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.