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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A mild and efficient method for the synthesis of vinylogous carbamates from alkyl azides
TL;DR: In this paper, a mild and efficient one-pot method for the synthesis of vinylogous carbamates is reported starting from alkyl azides under a hydrogen atmosphere using 10% Pd/C.
Journal ArticleDOI
Asymmetric synthesis of a tetracyclic model for the aziridinomitosenes
TL;DR: In this article, a model for the fundamental structure of aziridinomitosenes has been constructed by using a reformatsky reaction on a thiolactam precursor and Heck cyclisation of 13 to form the indole ring.
Journal ArticleDOI
One-pot synthesis of aminoenone via direct reaction of the chloroalkyl enone with NaN3: rapid access to polycyclic alkaloids.
TL;DR: A new one-pot procedure for the preparation of aminoenone from chloroalkyl enone and sodium azide was demonstrated and the structure of the presumed triazoline intermediate in this process was confirmed by X-ray analysis for the first time.
Journal ArticleDOI
Influence of ring size on the outcome of sulfide contraction reactions with thiolactams. Isolation of bicyclic ketene S,N-acetals and thioisomünchnones
TL;DR: In this paper, the reaction between diethyl bromomalonate and 3-phenylpyrrolidine-2-thione yielded a vinylogous urethane by the Eschenmoser sulfide contraction.
Journal ArticleDOI
New aromatic annulation reaction via a C14 enaminone synthon: synthesis of ‘terpenoid-like chalcones’
TL;DR: In this paper, a new annulation reaction of a C-14 compound with several anions led to new terpenoid-like chalcones, which were easily obtained in a one-pot process starting from a compound derived from β-ionone.
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.