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Approaches Toward The Total Synthesis Of Oroidin Alkaloids
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Book Synopsis Approaches Toward the Total Synthesis of Oroidin Alkaloids by : Apsara K. Herath
Download or read book Approaches Toward the Total Synthesis of Oroidin Alkaloids written by Apsara K. Herath and published by . This book was released on 2020 with total page 96 pages. Available in PDF, EPUB and Kindle. Book excerpt: Nagelamides and ageliferin are oroidin-derived alkaloids which have gained the attention of the scientific community, because of their significant biological activity as well as the unprecedented structural diversity. Our work is directed toward the development of synthetic methods for the construction of oroidin dimers. Accordingly, this dissertation is composed of two sections; the chapter one provides an overview of the oroidin alkaloids with a particular focus on the nagelamide family and the third chapter describes synthetic studies towards ageliferin. The first part of chapter two focuses on the Palladium-catalyzed Stille cross-coupling reaction for the construction of the main dimeric scaffolds of the nagelamide molecules. First, we describe new methodology to synthesize the iodoimidazole fragment for use in the Stille cross-coupling reaction and subsequent progress in optimizing the yield of Stille reaction. Additional advancement of the synthesis has been achieved via azide installation in allylic and alkyl side chains of the basic framework of nagelamides A and C. A convenient method of dimethylaminosulfonyl group deprotection was reported on these advanced intermediates prior to the installation of pyrrole carboxamide moieties. The second part of chapter two details a novel approach for acylation was developed in azidecontaining imidazole systems using thio acid chemistry providing amides in one step. The reaction conditions were optimized in diverse monomeric imidazole containing-azide systems, and excellent yields of acetamide and benzamide formation were obtained. Interestingly, a newly synthesized pyrrole thio acid offers promising results for the installation of the pyrrole carboxamide moiety in oroidin-derived systems. This chemistry can be employed in the final transformation of nagelamide A and C to install the pyrrole carboxamide moieties, however; the final reaction conditions still require optimization. The third chapter describes a potential intermediate en route to ageliferin which was constructed through an intramolecular Diels-Alder reaction using 4-vinylimidazole tethered to a urazole as the starting material. The Diels-Alder precursor was synthesized through palladium-catalyzed TsujiTrost cross-coupling reaction between t-butyl carbonate protected vinylimidazole and Nphenylurazole in excellent yield. We have explored three different protecting groups (DMAS, Bn, and SEM) on the imidazole nitrogen which can affect both the Diels-Alder reactivity and the electronic nature of the tetrahydrobenzimidazole ring system. For example, this can influence the oxidative rearrangement and introduction of the C2-amino moiety at the later in the synthesis. Further studies are in progress to complete the total synthesis of ageliferin using these advanced intermediates.
Book Synopsis Application of Pd-catalyzed Reactions in the Total Synthsis of Oroidin-derived Alkaloids by : Manojkumar R. Bhandari
Download or read book Application of Pd-catalyzed Reactions in the Total Synthsis of Oroidin-derived Alkaloids written by Manojkumar R. Bhandari and published by . This book was released on 2014 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The oroidin family of marine natural products is a growing group of sponge-derived alkaloids which contain 2-aminoimidazole and pyrrolecarboxamide fragments as their signature features. Due to their structural diversity and biological activity, many groups are interested in the total synthesis of these natural products. It has been proposed that many of the alkaloids in this family are produced in nature simply by dimerization and/or cyclization of the simplest member, oroidin. In this dissertation we have attempted to explore these biosynthetic relationships to complete the total synthesis of several oridin-derived natural products. This dissertation consists of two parts. The first part describes the total synthesis of the nominal structure of nagelamide D and the development of approaches towards total synthesis of other congeners with the nagelamide family. The second part of this dissertation describes studies of intramolecular cyclization reactions of imidazolylpropargyl amides as linchpin synthons for the assembly of imidazole-containing natural products. In the first part, a Pd-catalyzed Stille reaction was used as a transformation to construct divinyl imidazole derivatives in convergent fashion. A divergent approach was used to further functionalize intermediates obtained from Stille reaction towards the total synthesis of several nagelamides. The total synthesis of nagelamide D was accomplished by using a double Mitsunobu reaction to install pyrrolecarboxamides. Selective hydrogenation of a trisubstituted olefin or electrocyclization reactions of divinyl intermediates obtained from the Stille reaction provided key frameworks required for the total synthesis of nagelamide A, nagelamide E and ageliferin respectively. Construction of the stereoisomeric Z-vinyl stannane provided access to the divinyl imidazole fragment required for the total synthesis of nagelamide C. In the second part, Pd-catalyzed and/or base promoted intramolecular cyclization reactions of imidazolylpropargyl amides were screened as a part of diversity oriented strategy for the assembly of natural product-like frameworks. Several novel heterocycles including morpholine, pyrazinone, oxazole, pyridinone and azepin derivatives were prepared using intramolecular cyclization. Many of these heterocyclic compounds have potential to serve as intermediates en route to the total synthesis of oroidin-derived alkaloids including stevensine, nagelamide R, nagelamide T, oxocyclostylidol, agelastatin A. The potential of this approach was demonstrated in a formal total synthesis of cyclooroidin.
Book Synopsis Some Approaches to the Total Synthesis of the Diterpenoid Alkaloids by :
Download or read book Some Approaches to the Total Synthesis of the Diterpenoid Alkaloids written by and published by . This book was released on 1964 with total page 167 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Approaches to the Total Synthesis of Furoquinoline Alkaloids by : Joseph Henry Cecil
Download or read book Approaches to the Total Synthesis of Furoquinoline Alkaloids written by Joseph Henry Cecil and published by . This book was released on 1967 with total page 98 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Approaches Towards the Total Synthesis of the Ephedradine Alkaloids by : G. R. Humphrey
Download or read book Approaches Towards the Total Synthesis of the Ephedradine Alkaloids written by G. R. Humphrey and published by . This book was released on 1987 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Approaches to the Total Synthesis of Alkaloid Natural Products Via Intramolecular Pericyclic Reactions by : Susan Yoshiko Tamura
Download or read book Approaches to the Total Synthesis of Alkaloid Natural Products Via Intramolecular Pericyclic Reactions written by Susan Yoshiko Tamura and published by . This book was released on 1983 with total page 254 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Approaches Toward the Total Synthesis of Uleine by : Leonard J. Calbo
Download or read book Approaches Toward the Total Synthesis of Uleine written by Leonard J. Calbo and published by . This book was released on 1966 with total page 149 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis An Approach to the Total Synthesis of Rhyncophylline by : Albert Harry Warfield
Download or read book An Approach to the Total Synthesis of Rhyncophylline written by Albert Harry Warfield and published by . This book was released on 1965 with total page 78 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Enantioselective Approach to Securinega Alkaloids by : David González Gálvez
Download or read book Enantioselective Approach to Securinega Alkaloids written by David González Gálvez and published by . This book was released on 2009 with total page 221 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Part I. General Approach to the Total Synthesis of 9-methoxy Substituted Indole Alkaloids by : Jun Ma
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:
Book Synopsis Chemoenzymatic Approaches to Montanine Alkaloids by : Okanya John Kokas
Download or read book Chemoenzymatic Approaches to Montanine Alkaloids written by Okanya John Kokas and published by . This book was released on 2007 with total page 238 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Approaches to the Biogenetically Patterned Synthesis of Amaryllidaceae Alkaloids by : Steven William Scott
Download or read book Approaches to the Biogenetically Patterned Synthesis of Amaryllidaceae Alkaloids written by Steven William Scott and published by . This book was released on 1972 with total page 198 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Strategies and Tactics in Organic Synthesis by : Gopal Sirasani
Download or read book Strategies and Tactics in Organic Synthesis written by Gopal Sirasani and published by Elsevier Inc. Chapters. This book was released on 2013-07-29 with total page 39 pages. Available in PDF, EPUB and Kindle. Book excerpt: Described herein is an account of my laboratory’s entry into the magnificent field of complex alkaloid total synthesis, spanning the development of novel methods for quickly assembling polycyclic frameworks through the total synthesis of various members of the Strychnos alkaloids. A discussion of the prior art related to our approach to these alkaloids in addition to strategic decisions and reasoning made en route to targets akuammicine ( 1 ), strychnine ( 2 ), and leuconicines A ( 3 ) and B ( 4 ) is carefully detailed. Finally, we present the retrosynthetic analyses of the aforementioned targets and respective total syntheses thereof (including asymmetric variants).
Book Synopsis Synthesis of Indolizidine Alkaloids Via the Intramolecular Acylnitroso Diels-Alder Reaction by : Duane R. Romer
Download or read book Synthesis of Indolizidine Alkaloids Via the Intramolecular Acylnitroso Diels-Alder Reaction written by Duane R. Romer and published by . This book was released on 1990 with total page 296 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis New methods of alkaloid synthesis by : Thomas Allen Puckette
Download or read book New methods of alkaloid synthesis written by Thomas Allen Puckette and published by . This book was released on 1980 with total page 308 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Recent Applications of Selected Name Reactions in the Total Synthesis of Alkaloids by : Majid M. Heravi
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
Book Synopsis Part A, Synthesis of the C1-C27 Subunit of the Aplyronines by : Jianguang Zhou
Download or read book Part A, Synthesis of the C1-C27 Subunit of the Aplyronines written by Jianguang Zhou and published by . This book was released on 2005 with total page 600 pages. Available in PDF, EPUB and Kindle. Book excerpt:
