General approach to halogenated tetrahydrofuran natural products from red algae of the genus Laurencia. Total synthesis of (.+-.)-trans-kumausyne and demonstration of an asymmetric synthesis strategy

1991 ◽  
Vol 113 (14) ◽  
pp. 5378-5384 ◽  
Author(s):  
Mark J. Brown ◽  
Timothy Harrison ◽  
Larry E. Overman
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Red Algae ◽  
Synthesis Strategy

scholarly journals Heronapyrrole D: A case of co-inspiration of natural product biosynthesis, total synthesis and biodiscovery

2014 ◽  
Vol 10 ◽  
pp. 1228-1232 ◽  
Author(s):  
Jens Schmidt ◽  
Zeinab Khalil ◽  
Robert J Capon ◽  
Christian B W Stark
Keyword(s):  
Antibacterial Activity ◽  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Natural Product ◽  
Joint Effort ◽  
Natural Product Biosynthesis ◽  
New Members ◽  
Degree Of Oxidation ◽  
Rare Class

The heronapyrroles A–C have first been isolated from a marine-derived Streptomyces sp. (CMB-0423) in 2010. Structurally, these natural products feature an unusual nitropyrrole system to which a partially oxidized farnesyl chain is attached. The varying degree of oxidation of the sesquiterpenyl subunit in heronapyrroles A–C provoked the hypothesis that there might exist other hitherto unidentified metabolites. On biosynthetic grounds a mono-tetrahydrofuran-diol named heronapyrrole D appeared a possible candidate. We here describe a short asymmetric synthesis of heronapyrrole D, its detection in cultivations of CMB-0423 and finally the evaluation of its antibacterial activity. We thus demonstrate that biosynthetic considerations and the joint effort of synthetic and natural product chemists can result in the identification of new members of a rare class of natural products.

scholarly journals α-Ketol and α-iminol rearrangements in synthetic organic and biosynthetic reactions

2021 ◽  
Vol 17 ◽  
pp. 2570-2584
Author(s):  
Scott Benz ◽  
Andrew S Murkin
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Hydroxy Group ◽  
Tandem Reactions ◽  
Aryl Group ◽  
The Past

In the presence of a suitable acid or base, α-hydroxyaldehydes, ketones, and imines can undergo isomerization that features the 1,2-shift of an alkyl or aryl group. In the process, the hydroxy group is converted to a carbonyl and the aldehyde/ketone or imine is converted to an alcohol or amine. Such α-ketol/α-iminol rearrangements are used in a wide variety of synthetic applications including asymmetric synthesis, tandem reactions, and the total synthesis and biosynthesis of natural products. This review explores the use of α-ketol rearrangements in these contexts over the past two decades.

Catalytic asymmetric preparation of pyrroloindolines: strategies and applications to total synthesis

2021 ◽  
Author(s):  
Guang-Jian Mei ◽  
Wai Lean Koay ◽  
Chuan Xiang Alvin Tan ◽  
Yixin Lu
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
State Of The Art ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric

Pyrroloindolines are widely present in natural products. In this review, we summarize state-of-the-art of catalytic asymmetric synthesis of pyrroloindolines, as well as related applications to natural products total synthesis.

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 Catalytic asymmetric synthesis of biologically important 3-hydroxyoxindoles: an update

2016 ◽  
Vol 12 ◽  
pp. 1000-1039 ◽  
Author(s):  
Bin Yu ◽  
Hui Xing ◽  
De-Quan Yu ◽  
Hong-Min Liu
Keyword(s):  
Clinical Trials ◽  
Natural Products ◽  
Drug Discovery ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Biological Activities ◽  
Transition Metal Catalysis ◽  
Metal Catalysis ◽  
Catalytic Asymmetric Synthesis ◽  
Catalytic Asymmetric

Oxindole scaffolds are prevalent in natural products and have been recognized as privileged substructures in new drug discovery. Several oxindole-containing compounds have advanced into clinical trials for the treatment of different diseases. Among these compounds, enantioenriched 3-hydroxyoxindole scaffolds also exist in natural products and have proven to possess promising biological activities. A large number of catalytic asymmetric strategies toward the construction of 3-hydroxyoxindoles based on transition metal catalysis and organocatalysis have been reported in the last decades. Additionally, 3-hydroxyoxindoles as versatile precursors have also been used in the total synthesis of natural products and for constructing structurally novel scaffolds. In this review, we aim to provide an overview about the catalytic asymmetric synthesis of biologically important 3-substituted 3-hydroxyoxindoles and 3-hydroxyoxindole-based further transformations.

scholarly journals The Invention of New Methodologies: An Opportunity for Dating Natural Products

Synlett ◽  
2018 ◽  
Vol 29 (16) ◽  
pp. 2108-2116 ◽  
Author(s):  
Louis Fensterbank ◽  
Marion Barbazanges
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Carboxylic Acids ◽  
Sulfur Atom ◽  
Radical Chemistry ◽  
Coinage Metals ◽  
New Methodologies ◽  
Homolytic Substitution

This Account surveys almost two decades of methodological developments and their straightforward applications to the total synthesis of simple natural products. The main directions covered include radical chemistry and cascades, electrophilic catalysis based on coinage metals, and asymmetric synthesis based on bis(sulfoxides) auxiliaries.1 Introduction2 Radical Cascades2.1 N-Cyanamides2.2 Homolytic Substitution at Sulfur Atom to Give Sultines3 Electrophilic Catalysis Based on Platinum(II) and Gold(I) Complexes4 From Alkylydene Bis(sulfoxides) to Chiral Carboxylic Acids5 Conclusion and Perspectives

scholarly journals Unified divergent strategy towards the total synthesis of the three sub-classes of hasubanan alkaloids

2021 ◽  
Vol 12 (1) ◽  
Author(s):  
Guang Li ◽  
Qian Wang ◽  
Jieping Zhu
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Asymmetric Synthesis ◽  
Michael Addition ◽  
Total Syntheses ◽  
Bond Forming ◽  
The Past ◽  
Tricyclic Compounds

AbstractElegant asymmetric synthesis of hasubanan alkaloids have been developed over the past decades. However, a divergent approach leading to all three sub-classes of this family of natural products remains unknown. We report herein the realization of such an endeavor by accomplishing enantioselective total syntheses of four representative members. The synthesis is characterized by catalytic enantioselective construction of the tricyclic compounds from which three different intramolecular C-N bond forming processes leading to three topologically different hasubanan alkaloids are developed. An aza-Michael addition is used for the construction of the aza-[4.4.3]-propellane structure of (-)-cepharamine, whereas an oxidation/double deprotection/intramolecular hemiaminal forming sequence is developed to forge the bridged 6/6/6/6 tetracycle of (-)-cepharatines A and C and a domino bromination/double deprotection/cyclization sequence allows the build-up of the 6/6/5/5 fused tetracyclic structure of (−)-sinoracutine.

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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