ChemInform Abstract: Chromium in Organic Synthesis. From Methodology to Total Synthesis of Natural Products

ChemInform ◽  
2010 ◽  
Vol 41 (1) ◽  
pp. no-no
Author(s):  
Rachid Baati ◽  
John R. Falck ◽  
Charles Mioskowski
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis

Organic synthesis with tricarbonyliron lactone complexes

1988 ◽  
Vol 326 (1592) ◽  
pp. 633-640 ◽  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Selective Oxidation ◽  
Organic Synthesis ◽  
Lewis Acids ◽  
Iron Carbonyl ◽  
Organic Substrates ◽  
Carpenter Bee

π-Ally tricarbonyliron lactone complexes are useful precursors for organic synthesis. These stable complexes are readily prepared from a variety of organic substrates and may be respectively converted to β- and δ-lactones by selective oxidation or exhaustive carbonylation. The natural products massoialactone, parasorbic acid, the carpenter bee pheromone and malyngolide were prepared by using the iron carbonyl methodology, along with precursors for the ionophore antibiotic CP 61405 and avermectin B1a synthesis. Several corresponding lactam complexes were obtained by treatm ent of the π-allytricarbonyliron lactones with amines in the presence of Lewis acids. These complexes were used in the formal total synthesis of the nocardicins and ( + )-thienamycin.

Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products

2013 ◽  
Vol 85 (4) ◽  
pp. 741-753 ◽  
Author(s):  
Hee-Yoon Lee ◽  
Seog-Beom Song ◽  
Taek Kang ◽  
Yoon Jung Kim ◽  
Su Jeong Geum
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Reactive Intermediates ◽  
Diazo Compounds ◽  
Tandem Reaction ◽  
Cycloaddition Reactions ◽  
Free Radical Reactions ◽  
Sulfur Ylide ◽  
Epoxide Formation

Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.

scholarly journals Evolution of Pauson-Khand Reaction: Strategic Applications in Total Syntheses of Architecturally Complex Natural Products (2016–2020)

Catalysts ◽  
2020 ◽  
Vol 10 (10) ◽  
pp. 1199
Author(s):  
Sijia Chen ◽  
Chongguo Jiang ◽  
Nan Zheng ◽  
Zhen Yang ◽  
Lili Shi
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Organic Synthesis ◽  
Total Syntheses

Metal-mediated cyclizations are important transformations in a natural product total synthesis. The Pauson-Khand reaction, particularly powerful for establishing cyclopentenone-containing structures, is distinguished as one of the most attractive annulation processes routinely employed in synthesis campaigns. This review covers Co, Rh, and Pd catalyzed Pauson-Khand reaction and summarizes its strategic applications in total syntheses of structurally complex natural products in the last five years. Additionally, the hetero-Pauson-Khand reaction in the synthesis of heterocycles will also be discussed. Focusing on the panorama of organic synthesis, this review highlights the strategically developed Pauson-Khand reaction in fulfilling total synthetic tasks and its synthetic attractiveness is aimed to be illustrated.

ChemInform Abstract: Aziridinyl Imines in Organic Synthesis: Development of Tandem Reaction Strategies and Application to Total Synthesis of Natural Products

ChemInform ◽  
2013 ◽  
Vol 44 (36) ◽  
pp. no-no
Author(s):  
Hee-Yoon Lee ◽  
Seog-Beom Song ◽  
Taek Kang ◽  
Yoon Jung Kim ◽  
Su Jeong Geum
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Tandem Reaction

Preface

2005 ◽  
Vol 77 (7) ◽  
pp. iv
Author(s):  
Tamejiro Hiyama
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Organic Synthesis ◽  
Molecular Assembly ◽  
Biologically Active ◽  
Synthetic Methods ◽  
Scientific Program ◽  
Organometallic Catalysts ◽  
The Impact

Organic synthesis has long played a pivotal role in the chemical sciences. It is therefore unsurprising and appropriate that the International Conferences on Organic Synthesis (ICOS) continue to thrive. This series was initiated by IUPAC in 1976 and has since featured biennially as one of the core events of the Union. What is surprising is that 22 years have elapsed since an ICOS event was last hosted by Japan. On that occasion, ICOS-4 was held in 1982 at Shinjuku, Tokyo, and was acclaimed as a great success. The latest event (ICOS-15), in Nagoya, Japan on 1ñ6 August 2004, offered an opportunity to match or surpass the impact of its predecessoróa challenge that was taken up enthusiastically under the leadership of Profs. Minoru Isobe (Nagoya University) and Hisashi Yamamoto (now at the University of Chicago) as Conference co-Chairs. Almost 1000 participants converged on Nagoya from all parts of the world. A noticeably high level of participation by delegates from East Asia in relation to those from North America and Europe attested to the growing capacity of this region to contribute to research at the forefront of this area of the chemical sciences. The scientific program of the Conference embraced all aspects of modern synthetic organic chemistry, inter alia, the invention of selective synthetic methods, asymmetric synthesis, total synthesis of natural products, design and synthesis of artificial agents for pharmaceutical and agricultural uses, and molecular assembly and materials based on molecular function. This topical breadth was also captured in a poster program, which was handsomely supported by no less than 466 displays on every conceivable facet of the subject. Overall, it is evident that organic synthesis has expanded its boundaries increasingly toward biological and material sciences, in response to the new challenges arising from rapid progress in molecular biology and applied physics during recent years.A lecture program comprising 10 plenary and 20 invited presentations, in addition to the Thieme/IUPAC award lecture and two Nagoya medal lectures, contributed to a truly exciting Conference experience, and the 21 speakers who kindly agreed to contribute papers based upon their presentations have made it possible to capture some of the excitement in this issue of Pure and Applied Chemistry. The Nagoya Gold Medallist, J. F. Stoddart, used the occasion to share an absorbing and very personal perspective on molecular assembly and materials, a theme on which M. Fujita also disclosed new insights and developments. The perennial theme of total synthesis of natural products, provided scope for presentation of highly creative accomplishments by S. Ley, J. Cossy, Y. Langlois, R. Pilli, and S. Kozmin on a variety of challenging targets. Such advances in the total synthesis of biologically active natural products having extremely complex structures, often necessitate development of novel synthetic methods, and H. Overkleeft, P. Chiu, V. Nair, T.-P. Loh, S. Martin, T.-Y. Luh, E. Juaristi, and M. Catellani did justice to this theme with presentations on a variety of extremely elegant and sophisticated new developments in methodology, based upon organometallic catalysts and/or reagents. Finally, the broad theme of asymmetric synthesis using organometallic complexes with chiral ligands or chiral organocatalysts was developed in conjunction with combinatorial methodology, which is shown to be highly effective in optimizing catalytic systems. Those who contributed to the topic of asymmetric synthesis are K. Ding, A. Charette, S. H. Kang, A. Berkessel, and K. Maruoka, the recipient of the Nagoya Silver Medal.What is the future of organic synthesis? The invention of unprecedented drugs and materials has enriched and expanded the horizons of the human experience in formerly unimagined ways, and owes much to the ever increasing ingenuity of organic synthesis, and recognition and attainment of new synthetic targets. The impact of organic synthesis on cognate disciplines and on general advancement of science and technology is definitely enormous and will be further strengthened by future challenges and opportunities. Thus, it is hoped that younger generations will be inspired to participate in tapping this rich potential, in the cause of advancing science and contributing to the enrichment of future life. These aspirations may yield incalculable rewards. Such progress will certainly be reflected in the scientific program of the next Conference in the ICOS series, which will take place in Merida, Yucatan, Mexico on 11ñ15 June 2006, under the chairmanship of Dr. Eusebio Juaristi, Instituto Politecnico Nacional, Mexico.Tamejiro HiyamaConference EditorDepartment of Material ChemistryKyoto University, Kyoto, Japan *An issue of reviews and research papers based on lectures presented at the 15th International Conference on Organic Synthesis (ICOS-15), held in Nagoya, Japan, 1-6 August 2004, on the theme of organic synthesis. Other presentations are published in this issue, pp. 1087-1296.

scholarly journals The endeavor of total synthesis and its impact on chemistry, biology and medicine

2014 ◽  
Vol 1 (2) ◽  
pp. 233-252 ◽  
Author(s):  
K. C. Nicolaou ◽  
Christopher R. H. Hale
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Present State ◽  
Method Development ◽  
Complex Molecules ◽  
Total Syntheses ◽  
Target Molecule ◽  
Living Nature ◽  
Medical Relevance

Abstract The synthesis of urea in 1828 set in motion the discipline of organic synthesis in general and of total synthesis in particular, the art and science of synthesizing natural products, the molecules of living nature. Early endeavors in total synthesis had as their main objective the proof of structure of the target molecule. Later on, the primary goal became the demonstration of the power of synthesis to construct complex molecules through appropriately devised strategies, making the endeavor an achievement whose value was measured by its elegance and efficiency. While these objectives continue to be important, contemporary endeavors in total synthesis are increasingly focused on practical aspects, including method development, efficiency, and biological and medical relevance. In this article, the emergence and evolution of total synthesis to its present state is traced, selected total syntheses from the author's laboratories are highlighted, and projections for the future of the field are discussed.

scholarly journals α-C(sp3)-H Arylation of Cyclic Carbonyl Compounds

2021 ◽  
Author(s):  
Mei Wang ◽  
Wei Wang ◽  
Dashan Li ◽  
Wen-Jing Wang ◽  
Rui Zhan ◽  
...  
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Crucial Role ◽  
Carbonyl Compounds ◽  
High Efficiency ◽  
Cyclic Ketones ◽  
Important Type

Abstractα-C(sp3)-H arylation is an important type of C-H functionalization. Various biologically significant natural products, chemical intermediates, and drugs have been effectively prepared via C-H functionalization. Cyclic carbonyl compounds comprise of cyclic ketones, enones, lactones, and lactams. The α-C(sp3)-H arylation of these compounds have been exhibited high efficiency in forming C(sp3)-C(sp2) bonds, played a crucial role in organic synthesis, and attracted majority of interests from organic and medicinal communities. This review focused on the most significant advances including methods, mechanism, and applications in total synthesis of natural products in the field of α-C(sp3)-H arylations of cyclic carbonyl compounds in recent years.

scholarly journals Recent applications of intramolecular Diels–Alder reaction in total synthesis of natural products

RSC Advances ◽  
2015 ◽  
Vol 5 (63) ◽  
pp. 50890-50912 ◽  
Author(s):  
Majid M. Heravi ◽  
Vaezeh Fathi Vavsari
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Cycloaddition Reaction ◽  
Alder Reaction ◽  
Diels Alder ◽  
Diels Alder Reaction

Diels–Alder (D–A) reaction is undoubtedly the most powerful [4 + 2] cycloaddition reaction in organic synthesis.

Synthesis of chiral propargyl alcohols following the base-induced elimination protocol: application in the total synthesis of natural products

2020 ◽  
Vol 44 (13) ◽  
pp. 4972-4986
Author(s):  
Uma Maheshwar Gonela ◽  
Jhillu S. Yadav
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Enantiomerically Pure ◽  
Propargyl Alcohols

Synthesis of enantiomerically pure propargyl alcohols is one of the most important tools in organic synthesis and “base-induced elimination of β-alkoxy chlorides” could offer the enantiomerically pure propargyl alcohols.

scholarly journals Divergent Strategy in Marine Tetracyclic Meroterpenoids Synthesis

Marine Drugs ◽  
2021 ◽  
Vol 19 (5) ◽  
pp. 273
Author(s):  
Antonio Rosales Martínez ◽  
Ignacio Rodríguez-García ◽  
Josefa L. López-Martínez
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Natural Product ◽  
Organic Synthesis ◽  
Late Stage ◽  
Marine Natural Product ◽  
Synthesis Strategy ◽  
Related Compounds

The divergent total synthesis strategy can be successfully applied to the preparation of families of natural products using a common late-stage pluripotent intermediate. This approach is a powerful tool in organic synthesis as it offers opportunities for the efficient preparation of structurally related compounds. This article reviews the synthesis of the marine natural product aureol, as well as its use as a common intermediate in the divergent synthesis of other marine natural and non-natural tetracyclic meroterpenoids.

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