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Author : Friedrich K. Hess
Publisher :
ISBN 13 :
Total Pages : 0 pages
Book Rating : 4.:/5 (871 download)
Download or read book An Approach to the Synthesis of Lycopodium Alkaloids written by Friedrich K. Hess and published by . This book was released on 1963 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : George Alexander Cooke
Publisher :
ISBN 13 :
Total Pages : 0 pages
Book Rating : 4.:/5 (143 download)
Download or read book An Approach to the Synthesis of Lycopodium Alkaloids written by George Alexander Cooke and published by . This book was released on 1964 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt: The compound N-acetyl-2-chloro-2-(3~aminopropyl)- cyclohexanone (LXXXI) has been prepared by the alkylation of the pyrrolidine enamine of cyclohexanone, followed by hydride reduction of the corresponding ethylene ketal, acetylation, hydrolysis of the ketal, and chlorination of the resulting N-acetyl ketone. In a more direct approach to a lycopodine system, a series of hexahydrojulolidine derivatives, oxygenated at C-9 and carrying a substituent at C-ll, were prepared. Thus Birch reduction of 9-methoxyjulolidine XXVIII yielded the dihydro-derivative XXXVI which on treatment with ethylene glycol and perchloric acid was converted to the ethylene-ketal iminium perchlorate XCVIII, This substance was then subjected to the conditions of the Grignard reaction using methallyl magnesium chloride (CVII) to produce the corresponding C-ll adduct as two stereoisomers CX (all trans) and CXI (all cis), the latter being the major product. Pure CXI was obtained by column chromatography and experiments were carried out to deter-* mine its stereochemistry. Treatment of the CXI (as its perchlorate) with ozone followed by catalytic reduction of the ozonide produced the ketone CXXIII and several attempts were made to convert this to the annotinine II skeleton by photochemical methods. Reactions were as well performed designed to introduce unsaturation at C-7a, 8 thus providing a compound which might be expected to produce the cis-trans isomer (CXLIV) on dissolving metal reduction> The mass spectra of several of these derivatives were measured and are interpreted by analogy with fragmentations observed in several Lycopodium alkaloids.
Author : Gregory Wayne Schwing
Publisher :
ISBN 13 :
Total Pages : 140 pages
Book Rating : 4.:/5 (319 download)
Download or read book A Biogenetic Approach to the Synthesis of the Lycopodium Alkaloids written by Gregory Wayne Schwing and published by . This book was released on 1972 with total page 140 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Jerold Steven Horn
Publisher :
ISBN 13 :
Total Pages : 150 pages
Book Rating : 4.:/5 (361 download)
Download or read book Lycopodium Alkaloids written by Jerold Steven Horn and published by . This book was released on 1973 with total page 150 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Todd Andrew Blumenkopf
Publisher :
ISBN 13 :
Total Pages : 648 pages
Book Rating : 4.:/5 (29 download)
Download or read book Approaches to the Total Synthesis of the Lycopodium Alkaloid Fawcettimine and Related Studies written by Todd Andrew Blumenkopf and published by . This book was released on 1983 with total page 648 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Michael David Purdham
Publisher :
ISBN 13 :
Total Pages : 198 pages
Book Rating : 4.:/5 (35 download)
Download or read book Unified Approach to the Lycodine Lycopodium Alkaloids written by Michael David Purdham and published by . This book was released on 2008 with total page 198 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Sarah Elizabeth House
Publisher :
ISBN 13 :
Total Pages : 370 pages
Book Rating : 4.:/5 (868 download)
Download or read book A Unified Approach Toward the Total Synthesis of Lycopodium Alkaloids of the Miscellaneous Class written by Sarah Elizabeth House and published by . This book was released on 2010 with total page 370 pages. Available in PDF, EPUB and Kindle. Book excerpt: A unified approach to the total synthesis of Lycopodium alkaloids belonging to the miscellaneous class has been developed, wherein a single tetracyclic amine is employed as a common intermediate in synthetic studies toward several alkaloids. An overview of Lycopodium alkaloids is presented, including their structural classification, isolation and biological activity. The biosynthesis of alkaloids in the miscellaneous group is discussed in depth. A summary of previous synthetic work focusing on miscellaneous Lycopodium alkaloids is presented, including total syntheses of luciduline, lyconadins A and B and nankakurines A and B.A model study of spirolucidine is discussed. A biomimetic route to access spirolucidine and nankakurine B has been investigated. In this study, a tetracyclic amine that is a key intermedite in the total synthesis of lyconadin A previously developed in our laboratory is elaborated into a tertiary alcohol that mimics the proposed biosynthetic precursor of nankakurine B.A biomimetic ring-contractive [alpha]-hydroxyimine rearrangement to generate nankakurine B has been extensively investigated and found to be disfavored. The conversion of a tricyclic ketone (first synthesized en route to lyconadin A) to the tetracyclic core of serratezomine D has been investigated. The core of this molecule was inaccessible via methods employed in the studies toward lyconadin A. The total synthesis of 1'-epi-dihydrolycolucine from the key common tetracyclic amine intermediate has been achieved. Studies toward the synthesis of serratezomine E served as a platform to develop this method and to determine the stereochemical outcome of this reaction.
Author : Barnett Bernstein
Publisher :
ISBN 13 :
Total Pages : 184 pages
Book Rating : 4.:/5 (133 download)
Download or read book Approaches to the Synthesis of Fawcettidine, a Lycopodium Alkaloid written by Barnett Bernstein and published by . This book was released on 1985 with total page 184 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Robert Andrew Ellison
Publisher :
ISBN 13 :
Total Pages : 200 pages
Book Rating : 4.:/5 (27 download)
Download or read book Synthesis of Lycopodium Alkaloids written by Robert Andrew Ellison and published by . This book was released on 1965 with total page 200 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Edward Fox Kleinman
Publisher :
ISBN 13 :
Total Pages : 350 pages
Book Rating : 4.:/5 (82 download)
Download or read book Total Synthesis of Lycopodium Alkaloids written by Edward Fox Kleinman and published by . This book was released on 1980 with total page 350 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Mrinmoy Saha
Publisher :
ISBN 13 :
Total Pages : 451 pages
Book Rating : 4.:/5 (897 download)
Download or read book A Unified Approach for the Total Synthesis of C10-functionalyzed Lycopodium Alkaloids written by Mrinmoy Saha and published by . This book was released on 2014 with total page 451 pages. Available in PDF, EPUB and Kindle. Book excerpt: Lycopodium alkaloids have shown widespread and noteworthy biological activity, consisting of over 250 known natural products. Moreover, their structural complexity and diversity have attracted considerable attention from numerous laboratories including our own. Recently, we have developed a unified approach that would provides access to numerous, previously unprepared C10-functionalized lycopodium alkaloids. The first enantioselective total syntheses of all C10-hydroxy lycopodium alkaloids have been accomplished. We have also made a significant progress towards himeradine A and other C10-functionlyzed pentacyclic lycopodium alkaloids. Key steps in the synthetic sequence towards C10-hydroxy lycopodium alkaloids include construction of six-membered ring using an organocatalyzed intramolecular Michael reaction, formation of tricyclic skeleton using a conformationally accelerated Mannich reaction and a tandem Oppenauer oxidation / aldol condensation cascade reaction to form the tetracyclic skeleton of the natural products. A proline sulfonamide catalyst has been explored and expanded for the intramolecular Michael reaction for the construction of common six-membered ring for all the C10-functionalized lycopodium alkaloids. During our endeavor towards the sis- membered ring formation it was observed that rate of the Michael reaction and conversion to product increases dramatically in presence of the proline sulfonamide catalyst. The effect of C10 stereochemistry (both R and S) was also explored in the Michael reaction and (R)-C10-epimer proved to give better diastereoselectivity during the process. A conformationally accelerated, intramolecular Mannich reaction route was utilized to the tricyclic skeleton of all C10-hydroxy lycopodium alkaloids to construct C4- C13. During the Mannich reaction the effect of C10 stereochemistry was explored as well and it was found that C4-C13 bond could only be formed with (R)-C10-epimer. In addition, protecting group on C10 alcohol has significant effect on the intramolecular Mannich reaction. We have accomplished the first enantioselective total synthesis of 10-hydroxylycopodine, deacetylpaniculine and paniculine. During our endeavor towards these natural products we have utilized an Oppenauer oxidation/aldol condensation cascade reaction to form the tetracyclic skeleton from the tricyclic intermediate. We have reported the first fully characterized NMR data for 10-hydroxylycopodine and optical rotation data for all the C10-hydroxy lycopodium alkaloids. Key aspects towards the C10-functionalyzed lycopodium alkaloids are Mander's reagent -mediated one carbon homologation, a tandem sulfone rearrangement / intramolecular Mannich cyclization to form the key tricyclic skeleton and synthesis of the advanced C10-alcohol intermediate towards the western portion of himeradine A. Additionally, the western portion of himeradine A will serve as the common intermediate towards related pentacyclic C10-functionalyzed lycopodium alkaloids. During the synthesis of the tricyclic C10-alcohol, several routes have been explored to functionalize the C4 center and finally the Mander's reagent strategy successfully installed the C3 ester. A significant tricyclic skeleton towards the pentacyclic C10-functionalyzed lycopodium alkaloids was achieved through utilization of a tandem 1,3-sulfone rearrangement/intramolecular Mannich reaction as the key steps. Polymer supported PPh3 was utilized to improve the yield of the Aza-Wittig / Mannich reaction sequence. We have discovered that the incorporation of the methyl-protecting group on C5-enol and reduction of the C3 ester to alcohol was necessary in order to successfully facilitate the C14-desulfurization.
Author : Hans-Joachim Knoelker
Publisher : Springer Science & Business Media
ISBN 13 : 3642255280
Total Pages : 268 pages
Book Rating : 4.6/5 (422 download)
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.-
Author : Rebecca Anne Murphy
Publisher :
ISBN 13 :
Total Pages : 340 pages
Book Rating : 4.:/5 (94 download)
Download or read book Toward the Synthesis of the Magellaninone- and Lycopladine-type Lycopodium Alkaloids written by Rebecca Anne Murphy and published by . This book was released on 2013 with total page 340 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes our strategy toward the synthesis of a variety of fawcettimine-type Lycopodium alkaloids. The first section focuses on the classification, structure, and historical significance of these natural products. This section also includes a proposal for their biosynthesis and a survey of the biological activities of the members of this class. The second section describes our work toward magellanine, magellaninone, and paniculatine. Two existing syntheses of these molecules are discussed, along with the strategy that we chose to employ in our work. We first pursue the synthesis of these natural products using a C4 pyridine C-H functionalization strategy that is based on precedent by the Fagnou and Echavarren groups. We then describe a C3 pyridine C-H functionalization approach that has more diverse methodological inspiration, although the original synthetic disconnection strategy derives from work done by the Jin Quan Yu group. Both of these synthetic endeavors are detailed herein. Finally, the third section covers our efforts toward the synthesis of lycopladines B, C, and D. We describe our "Heathcock-inspired"cascade approach toward the divergent synthesis of these three natural products. In this work, we have pursued the synthesis of a number of different substrates. We conclude with a summary of how this approach has evolved into a number of other projects within our group.
Author : James Newton
Publisher :
ISBN 13 :
Total Pages : 97 pages
Book Rating : 4.:/5 (919 download)
Download or read book Synthesis of Lycodine-Type Lycopodium Alkaloids Using C-H Functionalization Tactics written by James Newton and published by . This book was released on 2015 with total page 97 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes our syntheses of several lycodine-type Lycopodium alkaloids by the late-stage C-H functionalization of lycodine derivatives. Lycodine-type alkaloids are well-known for their neurological activity. For example, huperzine A is a potent acetylcholinesterase inhibitor and the complanadine family of molecules has been shown to induce the secretion of Nerve Growth Factor. Due to these properties, lycodine-type alkaloids serve as interesting lead compounds for the development of new therapies for neurodegenerative disorders, such as Alzheimer's disease. Unsurprisingly, these molecules have attracted the attention of the synthetic community. Chapter 1 reviews syntheses of lycodine-type Lycopodium alkaloids with particular emphasis on the syntheses of biologically active congeners. Chapter 2 describes our synthesis of complanadine B, an unsymmetrical dimer of lycodine, using two approaches. In the first, the requisite skeletal oxygenation was installed early in the synthetic sequence. Our second approach utilized a blocking group strategy to enable the late-stage oxygenation of the complanadine skeleton by preventing oxygenation at undesired sites. Chapter 3 describes our efforts toward the synthesis of the casuarinine family of Lycopodium alkaloids by the late-stage C-H functionalization of lycodine derivatives. Using this strategy, we have been able to complete the synthesis of casuarinine D and have made significant progress toward the synthesis of casuarinine H, which we believe can serve as an intermediate in the synthesis of several other lycodine-type alkaloids.
Author : Gisela Saborit Villarroya
Publisher :
ISBN 13 :
Total Pages : 162 pages
Book Rating : 4.:/5 (986 download)
Download or read book Development of a Divergent Strategy Towards the Synthesis of Lycopodium Alkaloids written by Gisela Saborit Villarroya and published by . This book was released on 2016 with total page 162 pages. Available in PDF, EPUB and Kindle. Book excerpt: En la present tesi doctoral s'ha desenvolupat una estratègia per obtenir els esquelets dels quatre alcaloides licopodi representatius a partir d'un mateix intermedi sintètic comú 1, de manera semblant al procés que té lloc a la natura. Com que tant la licopodina, la licodina com la fawcettimina tenen una configuració diferent al C-7 de la que presenta la flegmarina s'han preparat 20 grams del compost 2 de forma racèmica i s'ha dut a terme la separació dels dos enantiòmers per HPLC preparatiu. Per a la síntesi de la flegmarina ha sigut necessari transformar l'estructura de cis-decahidroquinolina de 2 en la trans decahidroquinolina de la flegmarina. A continuació s'ha addicionat un fosfonat de piridina i s'ha procedit a la hidrogenació de la vinil piridina en dues condicions diferents.
Author : Hans-Joachim Knölker
Publisher : Springer Science & Business Media
ISBN 13 : 3642255299
Total Pages : 268 pages
Book Rating : 4.6/5 (422 download)
Download or read book Alkaloid Synthesis written by Hans-Joachim Knölker and published by Springer Science & Business Media. This book was released on 2012-01-10 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.-
Author : Kathleen Tucker Hug
Publisher :
ISBN 13 :
Total Pages : 340 pages
Book Rating : 4.:/5 (29 download)
Download or read book Studies of the Stereoselectivity of the Mukaiyama Aldol Condensation and Approaches to the Total Synthesis of the Lycopodium Alkaloids Paniculatine and Magellanine written by Kathleen Tucker Hug and published by . This book was released on 1987 with total page 340 pages. Available in PDF, EPUB and Kindle. Book excerpt:
