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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Two-Component Method to Enantiopure Quinolizidinones and Indolizidinones. Total Synthesis of (−)-Lasubine II
TL;DR: The reaction of iodides 1 and enantiopure beta-amino esters 2 mediated by potassium carbonate in acetonitrile at 65 degrees C provides quinolizidinones or indolizodinones, together with piperidines or pyrrolidines 4, in high yields.
Journal ArticleDOI
Efficient Synthesis of β-Aminoacrylates and β-Enaminones Catalyzed by Zn(OAc)2·2H2O
TL;DR: In this article, the direct condensation of amines with β-ketoesters and β-diketones to produce functional enamine derivatives has been investigated with zinc Lewis acid catalysts.
Journal ArticleDOI
Addition of tethered nonaromatic carbon nucleophiles to chemoselectively activated amides.
TL;DR: This work successfully added silyl enol ethers, allylsilanes, and enamines to iminium ions generated from amides to create the first example of tethered nonaromatic carbon nucleophiles adding to activated amides for the generation of enaminals of various ring sizes, with endo- or ex-cyclic nitrogen.
Journal ArticleDOI
Vinylogous urethanes in alkaloid synthesis. Applications to the synthesis of racemic indolizidine 209B and its (5R*,8S*,8aS*)-(±) diastereomer, and to (−)-indolizidine 209B
TL;DR: In this paper, the synthesis of (5R*,8S*,8aS*) diastereomer (±)-20 was achieved in eight steps from pyrrolidine-2-thione and ethyl oct 2-enoate, using cyclisations exploiting the nucleophilicity of vinylogous urethanes derived from ethyl (2E)-{1]-1-[1-(2-hydroxyethyl)hexyl]pyrrolidin-2ylidene}acetate.
Journal ArticleDOI
The nonlinear optical properties of two dihydropyridones derived from curcumin.
TL;DR: Two dihydropyridone compounds are synthesized from curcumin using microwave radiation using the Fraunhofer approximation of the Fresnel-Kirchhoff diffraction with good quantitative and excellent qualitative agreements compared with experimental results.
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.