Recent Advances in the Total Synthesis of Piperidine and Pyrrolidine Natural Alkaloids with Ring‐Closing Metathesis as a Key Step
01 Oct 2003-European Journal of Organic Chemistry (John Wiley & Sons, Ltd)-Vol. 2003, Iss: 19, pp 3693-3712
TL;DR: The most recent applications of the ring-closing metathesis reaction (RCM) to construct piperidine and pyrrolidine cores for the total synthesis of natural alkaloids are described in this paper.
About: This article is published in European Journal of Organic Chemistry.The article was published on 2003-10-01. It has received 396 citations till now. The article focuses on the topics: Ring-closing metathesis & Piperidine.
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TL;DR: Examples of total syntheses in which metathesis reactions of olefins, enynes, and alkynes played a crucial role and which imparted to these endeavors certain elements of novelty, elegance, and efficiency are highlighted.
Abstract: With the exception of palladium-catalyzed cross-couplings, no other group of reactions has had such a profound impact on the formation of carbon-carbon bonds and the art of total synthesis in the last quarter of a century than the metathesis reactions of olefins, enynes, and alkynes. Herein, we highlight a number of selected examples of total syntheses in which such processes played a crucial role and which imparted to these endeavors certain elements of novelty, elegance, and efficiency. Judging from their short but impressive history, the influence of these reactions in chemical synthesis is destined to increase.
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TL;DR: Stereoselective Addition to N-Activated Pyridines James A. Bull, Guillaume Pelletier,† and Andre ́ B. Charette are credited for this work.
Abstract: Stereoselective Addition to N-Activated Pyridines James A. Bull,‡ James J. Mousseau, Guillaume Pelletier,† and Andre ́ B. Charette*,† †Department of Chemistry, Universite ́ de Montreál, P.O. Box 6128, Station Downtown, Montreál, Queb́ec, Canada H3C 3J7 ‡Department of Chemistry, Imperial College London, South Kensington, London SW7 2AZ, U.K. Department of Chemistry, Massachusetts Institute of Technology, 77 Massachusetts Avenue, Cambridge, Massachusetts 02139, USA
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References
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TL;DR: These air- and water-tolerant complexes were shown to exhibit an increased ring-closing metathesis activity at elevated temperature when compared to that of the parent complex 2 and the previously developed complex 3.
3,127 citations
TL;DR: In this paper, a review of recent advances in olefin metathesis focusing on the areas of ring-closing olefi cation (RCM) and cross-metathesis is presented.
1,877 citations
TL;DR: In this paper, the authors provide an overview of the development of catalysts for olefin metathesis which combine high activity, durability, and excellent tolerance towards polar functional groups.
Abstract: The advent of well-defined catalysts for olefin metathesis which combine high activity, durability, and excellent tolerance towards polar functional groups has revolutionized the field. The past decade has seen the rapid embrace of these reagents as tools for advanced organic and polymer chemistry and the success of this development is witnessed by a plethora of elegant applications to the synthesis of natural and nonnatural products. This review article provides an overview of these developments and intends to familiarize the reader with some very recent advances which hold the promise to expand the scope of the reaction even further. Moreover, the positive impact of metathesis on the fundamental logic of retrosynthetic planning is demonstrated by means of typical examples. Finally, it will be shown that metathesis is by no means restricted to alkenes as substrates, and some comments on metathesis reactions following unconventional mechanistic pathways will also be presented.
1,614 citations
TL;DR: From its characteristic ultraviolet absorption spectrum rapamycin can be classified as a triene and its activity is compared with that of amphotericin B, candicidin and nystatin.
Abstract: A streptomycete was isolated from an Easter Island soil sample and found to inhibit Candida albicans, Microsporum gypseum and Trichophyton granulosum. The antibiotic-producing microorganism was characterized and identified as Streptomyces hygroscopicus. The antifungal principle was extracted with organic solvent from the mycelium, isolated in crystalline form and named rapamycin. Rapamycin is mainly active against Candida albicans; minimum inhibitory concentration against ten strains ranged from 0.02 to 0.2 mug/ml. Its apparent activity against Microsporum gypseum and Trichophyton granulosum is lower because of its instability in culture media on prolonged incubation required by these fungi. No activity was observed against gram-positive and gram-negative bacteria. Acute toxicity in mice is low.
1,561 citations
TL;DR: The transition metal alkylidene-catalyzed olefin metathesis reaction and the related transition metal-mediated carbonyl olefination reaction are two such processes as discussed by the authors.
Abstract: Carbon-carbon bond forming reactions remain among the most important for the synthesis of organic structures. The transition metal alkylidene-catalyzed olefin metathesis reaction (eq 1) and the related transition metal alkylidene-mediated carbonyl olefination reaction (eq 2) are two such processes. Historically, olefin metathesis has been studied extensively both from the mechanistic standpoint and in the context of polymer synthesis. In contrast, its application to the synthesis of complex organic molecules and natural products has been limited. The related reaction, transition metal-mediated carbonyl olefination, is not as extensively studied mechanistically nor in synthetic applications. Among the reasons for this
gap in methodology has been the incompatibility of traditional catalysts with the polar functional groups
typically encountered in organic synthesis.
927 citations