Download or read book Total Synthesis of Tetracyclic Indole Alkaloids written by Martin Francis Jones and published by . This book was released on 1983 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Enantioselective Total Synthesis of arborescidine C and Related Tetracyclic Indole Alkaloids Using Organocatalysis written by 賽思 and published by . This book was released on 2017 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids written by Majid M. Heravi and published by Elsevier. This book was released on 2021-06-12 with total page 404 pages. Available in PDF, EPUB and Kindle. Book excerpt: Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids includes comprehensive coverage of name reactions in the synthesis of alkaloids. This book highlights the synthesis of various alkaloids using special name reactions including the Diels-Alder, Friedel-Crafts, Heck, Mannich, Pauson-Khand, Pictet-Spengler, Sonogashira and Suzuki reactions. In this book, some selected name reactions in the total synthesis of alkaloids are covered, as they can be used as the key step/steps in the synthesis of different alkaloids exhibiting various biological activities. All chapters include an introduction, history and mechanism of the name reaction, and present the origin of the natural product and its known biological activities. The pathway to total synthesis is visually illustrated, and the focus is on the step in which a name reaction is applied. Chemists working in the area of synthetic organic chemistry will find this reference useful, as well as those working to develop novel methodologies for the synthesis of natural products in both academia and industry. This book is also beneficial to biologists, pharmacists and botanists. Includes an introduction of alkaloids, their origins and biological properties Features the applications of special name reactions as the key step in the total synthesis of featured alkaloids Covers the pathway for the synthesis of alkaloids from commercially available or easily accessible starting materials by using at least one name reaction to achieve the desired target products
Download or read book Indole Alkaloids written by Maliha Uroos and published by Elsevier. This book was released on 2022-01-30 with total page 236 pages. Available in PDF, EPUB and Kindle. Book excerpt: Indole Alkaloids: Spirooxindole details the multistep synthesis of natural products using schematic diagrams, providing a quick-and-easy way to review and understand new and novel synthetic strategies to construct structural frameworks of natural products. As a volume in the Visual Guides to Natural Product Synthesis series, this book presents the schematic total syntheses of natural products containing a “spirooxindole” core structure. It covers spirooxindole molecules through visual diagrams, highlighting key steps involved in total, formal and semi-syntheses. Sections cover Brevianamide A and B, Citrinadin A and B, Coerulescine and Horsfiline, Elacomine and Isoelacomine, Gelsemine, Paraherquamide A and B, Rynchophylline, Isorynchophylline, and more. Visual layouts provide quick-and- easy access to developed synthetic routes towards the targeted spirooxindoles. Outlines synthetic strategies for natural products bearing a spirooxindole core structure Includes schematic diagrams of multistep synthetic routes, highlighting key steps along the way Describes all routes for the formal synthesis, semi-synthesis and total synthesis of spirooxindole alkaloids
Download or read book Total Synthesis of Indole Alkaloids written by Junpei Matsuoka and published by Springer Nature. This book was released on 2020-09-18 with total page 91 pages. Available in PDF, EPUB and Kindle. Book excerpt: This book explores efficient syntheses of indole alkaloids based on gold-catalyzed cascade cyclizations, presenting two strategies for total synthesis of these natural products based on gold-catalyzed reactions of conjugated diyne or ynamide. The book first describes the total and formal synthesis of dictyodendrins A–F based on direct construction of the pyrrolo[2,3-c]carbazole core using the gold-catalyzed annulation of azido-diynes and protected pyrrole. This synthetic strategy features late-stage functionalization of the pyrrolo[2,3-c]carbazole scaffold at several positions and allows diverse access to dictyodendrins and their derivatives. Secondly, the book discusses the formal synthesis of vindorosine based on the pyrrolo[2,3-d]carbazole construction using the gold-catalyzed cascade cyclization of ynamide. Importantly, the reaction using a chiral gold complex provides the optically active pyrrolo[2,3-d]carbazole. This strategy facilitates the rapid construction of the pyrrolocarbazole core structure of aspidosperma and related alkaloids, including vindorosine. These methodologies can accelerate the medicinal application of pyrrolocarbazole-type alkaloids and related compounds.
Download or read book The Total Synthesis of 16 17 dihydrosecodine and Related Indole Alkaloids written by Robert A. Farr and published by . This book was released on 1981 with total page 298 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Indole Alkaloids written by Rahman and published by CRC Press. This book was released on 1998-06-02 with total page 354 pages. Available in PDF, EPUB and Kindle. Book excerpt: Indole alkaloids constitute an important class of natural products which include a large number of pharmacologically important substances such as the anti-tumour alkaloids, vinblastine and vincristine, the blood pressure lowering substance reserpine, the hallucinatory lysergic acid and its derivatives, and the cardio-arrhythmic alkaloid, ajmalicine. This important field has attracted the leading synthetic organic chemists of the present century to develop synthetic approaches to the challenging structural architecture encountered in many indole alkaloids. The book describes the syntheses of various types of indole alkaloids.
Download or read book First Total Synthesis of and actinophyllic Acid and First Enantioselective Total Synthesis of Condylocarpine type Alkaloids written by Connor L. Martin and published by . This book was released on 2011 with total page 328 pages. Available in PDF, EPUB and Kindle. Book excerpt: Chapter 1. The unique indole alkaloid ( - )-actinophyllic acid (1) is introduced. Its biological activity, structural relationship to other indole alkaloids, and potential biosynthesis are discussed. Our plan for synthesizing ( - )-actinophyllic acid with the use of the aza-Cope/Mannich reaction as a key step is described in detail. Chapter 2. The first-generation total synthesis of (±)-actinophyllic acid (rac-1) is described. The central step in this synthesis is the aza-Cope/Mannich reaction, which constructs the core of the previously unknown hexacyclic ring system of actinophyllic acid from a much simpler tetracyclic precursor. The hexahydro-1,5-methano-1H-azocino[4,3-b]indole ketone rac-121 is assembled from o-nitrophenylacetic acid in four steps, with oxidative cyclization of the dienolate derivative of tricyclic precursor rac-119 being the pivotal step. In the most concise route, rac-121 is elaborated to allylic alcohol rac-130, which is transformed to pentacyclic ester rac-134 by a one-pot global deprotection-aza-Cope/Mannich-Fisher esterification sequence. In two additional steps, this intermediate is advanced to (±)-actinophyllic acid. Chapter 3. The second-generation total syntheses of (±)-actinophyllic acid (rac-1) and ( - )-actinophyllic acid (1) are described. The first-generation synthesis is streamlined by elaborating ketone rac-121 to B-hydroxyester intermediate rac-141, which is directly transformed to (±)-actinophyllic acid upon exposure to HCl and paraformaldehyde. This concise synthesis of (±)-actinophyllic acid is realized in 22% overall yield from commercially available di-tert-butyl malonate and o-nitrophenylacetic acid by a sequence that proceeds by way of only six isolated intermediates. The first enantioselective total synthesis of ( - )-actinophyllic acid (1) is accomplished by this direct sequence from tricyclic keto malonate (S)-119. Catalytic enantioselective reduction of enone 163 is the key step in the preparation of intermediate (S)-119 from the commercially available Boc-amino acid 161. Chapter 4. The first enantioselective total syntheses of indole alkaloids of the condylocarpine type are described. (+)-Condylocarpine (174a), (+)-isocondylocarpine (174b), and (+)-tubotaiwine (217) are prepared in high enantiomeric purity (>99% ee) from (1S,5R)-hexahydro-1,5-methano-1H-azocino[4,3-b]indole-12-one (1S,5R)-121 by way of five or six isolated intermediates.
Download or read book Part I General Approach to the Total Synthesis of 9 methoxy Substituted Indole Alkaloids written by Jun Ma and published by . This book was released on 2006 with total page 464 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Alkaloid Synthesis written by Hans-Joachim Knoelker and published by Springer Science & Business Media. This book was released on 2012-01-13 with total page 268 pages. Available in PDF, EPUB and Kindle. Book excerpt: Lycopodium Alkaloids: Isolation and Asymmetric Synthesis, by Mariko Kitajima and Hiromitsu Takayama.- Synthesis of Morphine Alkaloids and Derivatives, by Uwe Rinner and Tomas Hudlicky.- Indole Prenylation in Alkaloid Synthesis, by Thomas Lindel, Nils Marsch and Santosh Kumar Adla.- Marine Pyrroloiminoquinone Alkaloids, by Yasuyuki Kita and Hiromichi Fujioka.- Synthetic Studies on Amaryllidaceae and Other Terrestrially Derived Alkaloids, by Martin G. Banwell, Nadia Yuqian Gao, Brett D. Schwartz and Lorenzo V. White.- Synthesis of Pyrrole and Carbazole Alkaloids, by Ingmar Bauer and Hans-Joachim Knölker.-
Download or read book Total Synthesis of Indole Alkaloids written by Younggi Choi and published by . This book was released on 2003 with total page 678 pages. Available in PDF, EPUB and Kindle. Book excerpt: PART I. The preparation of (-)-ibogamine (1) in fourteen steps from benzoquinone and in 10% overall yield is a powerful illustration of the value of the asymmetric Diels-Alder reaction as a starting point in a multistep synthesis. All four cycloadducts, 70, 77, 84 and 96, obtained with the (S)-BINOL-TiCl2 complex were found to have the same absolute configuration. Furthermore, they are in the same enantiomeric series that Mikami observed with 1,4-naphthoquinone using the same catalyst, lending confidence to future stereochemical predictions that may be made with this system. PART II. Three different routes for the synthesis of the hexahydroisoquinoline 98 met obstacles which defeated our approach to koumine. The Diels-Alder reaction of cyclic 1-azadienes 102 and 108 was abandoned due to the lack of reactivity of the dienes. An anionic oxy-Cope rearrangement of the azabicyclo[2.2.2]octane system caused mainly decomposition of the starting materials. Finally, an intramolecular [2+2] photocycloaddition generated "crossed", "straight" and hydroisoquinoline products in varying ratios, depending on the substituent pattern of the substrate, but this approach was not synthetically useful. The results from this last study may be valuable for predicting the regiochemical outcome of certain intramolecular photocycloadditions.
Download or read book Total Synthesis of Natural Products written by Jie Jack Li and published by Springer Science & Business Media. This book was released on 2013-03-14 with total page 292 pages. Available in PDF, EPUB and Kindle. Book excerpt: 'Total Synthesis of Natural Products' is written and edited by some of today's leaders in organic chemistry. Eleven chapters cover a range of natural products, from steroids to alkaloids. Each chapter contains an introduction to the natural product in question, descriptions of its biological and pharmacological properties and outlines of total synthesis procedures already carried out. Particular emphasis is placed on novel methodologies developed by the respective authors and their research groups. This text is ideal for graduate and advanced undergraduate students, as well as organic chemists in academia and industry.
Download or read book Novel Approach to the Total Synthesis of Indole Alkaloids Via Cyclopentanoid Intermediates written by Mark Wingfield and published by . This book was released on 1982 with total page 91 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book TOTAL SYNTHESIS OF STRYCHNOS AND ASPIDOSPERMATAN ALKALOIDS written by Praveen Kokkonda and published by . This book was released on 2017 with total page 232 pages. Available in PDF, EPUB and Kindle. Book excerpt: The Strychnos class of indole alkaloids contain a pyrrolo[2,3-d]carbazole ABCE tetracyclic framework. The second-generation ABCE tetracycle approach was employed in the total synthesis of (±)-20-epi-lochneridine and progress toward total synthesis of (±)-alstolucine B. The second-generation approach featured Mitsunobu activation of the hydroxyethyl group in a gramine intermediate followed by intramolecular aza-Baylis-Hillman reaction. The substrate for hydroboration was redesigned to (±)-18-desmethyl akuammicine (1,1-disubstituted double bond), since the hydroboration of trisubstituted alkenes afforded tertiary alcohol via Markovnikov addition. The key steps were n-Bu3SnH mediated cyclization reaction to accomplish D-ring, tert-butyl hypochlorite indoline oxidation, and anti-Markovnikov hydroboration to introduce a primary alcohol. The total syntheses of Strychnos-Strychnos type bis-indole alkaloids (−)-leucoridine A and C were accomplished from the biomimetic dimerization of (−)-dihydrovalparicine. En route to (−)-dihydrovialparicine, known alkaloids (+)-geissoschizoline and (−)-dehydrogeissoschizoline were also prepared from commercially available N-tosyl indole 3-carboxaldehyde. Key steps consisted of an in situ dimerization of (−)-dihydrovalparicine from (−)-1, 2-dehydrogeissoschizoline with trifluoroacetic acid in the presence of 4 Å molecular sieves. Acid mediated ring-opening of the indolenine in (−)-leucoridine A to afford (−)-leucoridine C. DFT calculations were employed to elucidate the mechanism of dimerization, which suggested that a stepwise aza-Michael/spirocyclization sequence was preferred over the alternate hetero Diels-Alder cycloaddition reaction. A novel domino Michael/Mannich [4+2] annulation method was applied for concise total synthesis of Aspidospermatan alkaloids (+)-20-epi-condyfoline and progress toward the total synthesis of (+)-condyfoline. The additional key steps consisted of a LiHMDS mediated cyclization to form D-ring, dimethyl(methylthio)sulfonium tetrafluoroborate (DMTSF) mediated spirocyclization to form pentacyclic thioether and indoline oxidation with MnO2.
Download or read book Indole Ring Synthesis written by Gordon W. Gribble and published by John Wiley & Sons. This book was released on 2016-08-08 with total page 704 pages. Available in PDF, EPUB and Kindle. Book excerpt: Of the myriad of heterocycles known to man, the indole ring stands foremost for its remarkably versatile chemistry, its enormous range of biological activities, and its ubiquity in the terrestrial and marine environments. The indole ring continues to be discovered in natural products and to be employed in man-made pharmaceuticals and other materials. Given the enormous resurgence in indole ring synthesis over the past decade — highlighted by the power of transition metal catalysis — this authoritative guide addresses the need for a comprehensive presentation of the myriad of methods for constructing the indole ring, from the ancient to the modern, and from the obscure to the well-known. Following presentation of the classic indole ring syntheses and many newer methods, coverage continues with indole ring syntheses via pyrroles, indolines, oxindoles, isatins, radical and photochemical reactions, aryne cycloadditions. This extensive volume concludes with the modern transition metal–catalyzed indole ring syntheses that utilize copper, palladium, rhodium, gold, ruthenium, platinum, and other metals to fashion the indole ring Indole Ring Synthesis is a comprehensive, authoritative and up-to-date guide to the synthesis of this important heterocycle for organic chemists, pharmaceutical researchers and those interested in the chemistry of natural products.
Download or read book Synthetic Experiments in the Tetracyclic Indole Alkaloid Series written by Ian Glaisby Wright and published by . This book was released on 1965 with total page 310 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Part I Synthesis of the Tetracyclic Skeleton of the Lycopodium Alkaloid Lycopladine Hpart Ii Synthesis of the Tetracyclic Core of the Apparicine Class of Indole Alkaloids Via a Key Intermolecular Nitrosoalkene Conjugate Addition written by Pradeep Chauhan and published by . This book was released on 2015 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: AbstractPart IA synthesis of the tetracyclic framework 220 of the structurally unique Lycopodium alkaloid lycopladine H (21) has been achieved in 19 steps from phenol 60. A key step involved a novel double alkene hydroformylation/intramolecular reductive amination of 217 to form the azocane and spiropiperidine moieties of the natural product in the form of advanced tetracyclic intermediate 220 via intermediate dialdehyde 218. Disappointingly, we have been unable to convert this compound into the natural product. Part IIA convergent and concise synthetic route to the tetracyclic core 61 of the apparicine-type alkaloids has been achieved in only four steps in 80% overall yield from the known 3-formylindole ester 113 and 3-piperidone-derived [alpha]-chloroketoxime 80. Key transformations involve use of an intermolecular ester enolate/nitrosoalkene conjugate addition to form the C-15/16 bond of 117, followed by a reductive cyclization to form the C-ring of the tetracycle core 61, which has appropriate handles in place at C-16 and C-20, to easily access a number of the members of the apparicine class of indole alkaloids.
