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Author : Oscar Ortiz Escribano
Publisher :
ISBN 13 :
Total Pages : 356 pages
Book Rating : 4.:/5 (125 download)
Download or read book Synthetic Studies Towards the Marine Natural Product Amphidinolide H written by Oscar Ortiz Escribano and published by . This book was released on 2007 with total page 356 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Milena Kasprzyk
Publisher :
ISBN 13 :
Total Pages : 342 pages
Book Rating : 4.:/5 (387 download)
Download or read book Synthetic Studies Towards the Tridachione Family of Marine Natural Products written by Milena Kasprzyk and published by . This book was released on 2008 with total page 342 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Andrew P. Osnowski
Publisher :
ISBN 13 :
Total Pages : 0 pages
Book Rating : 4.:/5 (933 download)
Download or read book Studies Towards the Total Synthesis of the Amphidinolide C Family of Natural Products written by Andrew P. Osnowski and published by . This book was released on 2013 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Robert H. Bates
Publisher :
ISBN 13 :
Total Pages : 394 pages
Book Rating : 4.:/5 (763 download)
Download or read book Studies Toward the Total Synthesis of Amphidinolide C written by Robert H. Bates and published by . This book was released on 2009 with total page 394 pages. Available in PDF, EPUB and Kindle. Book excerpt: Amphidinolide C is one of the most biologically potent members of the amphidinolide family of natural products. Detailed in this thesis are studies toward the total synthesis of this complex macrolide. Three distinct syntheses of the C(1)-C(9) fragment are described. The first generation synthesis involves a diastereoselective chelate-controlled [3+2]-annulation reaction to form the C(3)-C(6) trans tetrahydrofuran. The second generation approach takes advantage of the C(4) methyl substituent to induce diastereoselectivity in an intramolecular hetero-Michael cyclization to form the same tetrahydrofuran. The third generation incorporates a non-chelate-controlled [3+2]-annulation reaction to afford the cis tetrahydrofuran product, followed by a base-promoted epimerization to the desired trans tetrahydrofuran. This route was accomplished in fewer steps than the first generation synthesis. Also described are stereoselective syntheses of the C(18)-C(34) C(10)-C(26) fragments of amphidinolide C, and the C(10)-C(29) fragment of amphidinolide F, a closely related natural product. Finally, a clear plan for the completion of the total synthesis of amphidinolide C is presented.
Author : Brian J. Myers
Publisher :
ISBN 13 :
Total Pages : 428 pages
Book Rating : 4.3/5 ( download)
Download or read book Studies Toward the Synthesis of the Amphidinolides written by Brian J. Myers and published by . This book was released on 2000 with total page 428 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Subham Mahapatra
Publisher :
ISBN 13 :
Total Pages : 639 pages
Book Rating : 4.:/5 (828 download)
Download or read book Part I: Total Synthesis of Marine Macrolide Amphidinolide F and Synthetic Studies Toward Amphidinolide C written by Subham Mahapatra and published by . This book was released on 2013 with total page 639 pages. Available in PDF, EPUB and Kindle. Book excerpt: More than 30 members of the diverse amphidinolide family of biologically active macrolides have been isolated over last three decades. From this family, amphidinolides C and F stand among the most complex and densely functionalized affiliates. Recently, we have accomplished the first total synthesis of amphidinolide F. The all-carbon framework of amphidinolide C has been synthesized. During endeavor toward the total syntheses of amphidinolides F / C, we have uncovered a "hidden symmetry element" present in the northern and southern domains of amphidinolides F / C. The southern C1-C and northern C1-C25 tetrahydrofuran segments were derived from a common intermediate. A scalable silver-catalyzed isomerization / cyclization on propargyl-benzoate / diol furnished the common intermediate in multigram quantity. The common intermediate provided access to over half of carbon backbone of the macrocycle as well as majority of stereochemistry present in amphidinolides F / C. Two strategically different techniques have been developed for the C9-C11 diene preparation. A metal-catalyst free Weinreb amide-vinyl lithium coupling / methylenation sequence furnished the diene motif. Alternately, diastereoselective addition of a dienyl iodide derived 2-lithio-1,3-diene species to an [alpha]-oxy aldehyde installed the C9-C11 diene and secured the C8 stereochemistry in single operation. The dienyl iodide was prepared via a regioselective hydrostannylation on an enyne. A challenging alkylation between an [alpha]-branched sulfone and an [alpha]-silyloxy iodide generated the all-carbon frameworks of amphidinolides F / C. An efficient oxidative desulfurization incorporated the carbonyl moiety at C15. The protecting group on C18 alcohol was found to have significant effect on the sulfone-iodide alkylation / oxidative desulfurization sequence. Installation of chelating ethoxyethyl ether on C18 alcohol helped the successful incorporation of C15 ketone and solved the deprotection problem in advanced stage of synthesis. A detailed analytical and computational study on proline sulfonamide-catalyzed aldol reactions has been performed. The pKa value of a proline sulfonamide catalyst was determined experimentally via NMR titration technique. Computational study revealed the origin of enhanced stereoselectivity by proline sulfonamide catalysts over parent proline. The non-classical hydrogen bonding interactions were found to be responsible for improved diastereoselectivity.
Author : Asunción Barbero
Publisher : MDPI
ISBN 13 : 3039284665
Total Pages : 182 pages
Book Rating : 4.0/5 (392 download)
Download or read book Synthetic and Biosynthetic Approaches to Marine Natural Products written by Asunción Barbero and published by MDPI. This book was released on 2020-03-24 with total page 182 pages. Available in PDF, EPUB and Kindle. Book excerpt: Marine natural products containing a heterocyclic moiety in their structure are present in a wide variety of sponges, corals, algae, and fungi. Many of them show important biological activities such as cytotoxic properties against several cancer cell lines. Their challenging chemical structures have attracted the attention of many researchers who have developed various synthetic approaches. This Special Issue presents some examples of new synthetic or biosynthetic methodologies to access this type of marine natural drug.
Author : Andrew Michael Lauer
Publisher :
ISBN 13 :
Total Pages : 241 pages
Book Rating : 4.:/5 (655 download)
Download or read book Studies Directed Toward the Synthesis of the B-type Amphidinolide Natural Products Using Nickel-catalyzed Reductive Couplings of Enynes and Carbonyl Compounds written by Andrew Michael Lauer and published by . This book was released on 2010 with total page 241 pages. Available in PDF, EPUB and Kindle. Book excerpt: Progress coupling of substrates, toward the total synthesis of amphidinolide B1 is described. The reductive 1,3-eynes and ketones was explored. It was found to work well with simple but failed to yield intermediates toward amphidinolide B1 [images] ... The coupling of 1,3-enyne and aldehyde fragments toward the synthesis of amphidinolides G3 and H4 is also described. The entire carbon skeleton of these natural products has been prepared from this coupling and a subsequent installation of a methyl group using an indium based reagent ... [images].
Author : Wei Zhang
Publisher :
ISBN 13 :
Total Pages : 660 pages
Book Rating : 4.:/5 (72 download)
Download or read book Synthetic Studies Toward the Total Synthesis of Amphidinolide B1 written by Wei Zhang and published by . This book was released on 2006 with total page 660 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : James Edward MacIntyre Booker
Publisher :
ISBN 13 :
Total Pages : 172 pages
Book Rating : 4.:/5 (125 download)
Download or read book Synthetic Studies Towards the Marine Natural Product Diazonamide A written by James Edward MacIntyre Booker and published by . This book was released on 2003 with total page 172 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : G. H. Churchill
Publisher :
ISBN 13 :
Total Pages : 388 pages
Book Rating : 4.:/5 (125 download)
Download or read book Synthetic Studies Towards the Marine Natural Product Diazonamide A written by G. H. Churchill and published by . This book was released on 2005 with total page 388 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Liang Lu
Publisher :
ISBN 13 :
Total Pages : 786 pages
Book Rating : 4.:/5 (436 download)
Download or read book Part I written by Liang Lu and published by . This book was released on 2010 with total page 786 pages. Available in PDF, EPUB and Kindle. Book excerpt: The structural architecture present in marine toxin azaspiracid - 20 stereocenters, 9 rings, 3 separated spirocenters - has attracted considerable synthetic attention. Our efforts toward the synthesis of azaspiracid have led to the completion of both C1-C26 northern and C27-C40 southern halves. Herein, the synthesis of southern FGHI ring system is described. The key steps included an Andrus anti-aldol coupling to furnish the C32, C33 stereocenters, an acid-catalyzed ketalization to furnish FG rings, and a Yb(OTf)3-mediated spiroaminal formation to generate I ring. The first total synthesis of cytotoxic macrolides amphidinolide B1 and the proposed structure of amphidinolide B2 have been accomplished. The key developed protocols include a metal catalyst-free sequence for the synthesis of the diene subunit, a non-chelation-controlled aldol coupling to install the C18 stereocenter, an efficient macrocyclization of the 26-membered lactone ring, and the incorporation of the labile allylic epoxide moiety. The unique structure of the highly substituted diene functionality represents significant synthetic challenges. A Wittig / HWE reaction sequence yielded the C13-C15 diene moiety in good yield in excellent diastereoselectivity. Subsequent Sharpless epoxidation and Red-Al-mediated regionselective epoxide opening gave the C16 tertiary alcohol. The protecting groups on C21 were discovered to have significant effects on the aldol reaction between C9-C18 aldehyde and C19-C25 methyl ketone. Although chelating groups such as PMB, Bn afforded 18S isomer as a single diastereomer, the removal of these groups has proven problematic. Non-chelating silyl group generated 18R isomer in 8:1 dr at -100°C, while the 18S stereomer was obtained at -40°C in 1.2:1 dr. A spontaneous intramolecular Wadsworth-Emmons olefination established the 26-membered macrocycle. The oxidation and in situ elimination of a selenide moiety proceeded smoothly in the presence of free alcohols using TMSOOTMS. The first total synthesis of amphidinolide B1 and the proposed structure of amphidinolide B2 were accomplished in 29 linear steps. Additionally, We discovered that the initially proposed structure of amphidinolide B2 was incorrect.
Author : Dewan S. Bhakuni
Publisher : Springer Science & Business Media
ISBN 13 : 1402034849
Total Pages : 397 pages
Book Rating : 4.4/5 (2 download)
Download or read book Bioactive Marine Natural Products written by Dewan S. Bhakuni and published by Springer Science & Business Media. This book was released on 2006-06-30 with total page 397 pages. Available in PDF, EPUB and Kindle. Book excerpt: Bioactive Marine Natural Products is the first book available that covers all aspects of bioactive marine natural products. It fills the void in the literature for bioactive marine natural products. The book covers various aspects of marine natural products and it is hoped that all the major classes of bioactive compounds are included. Different classes of marine organisms and the separation and isolation techniques are discussed. The chemistry and biology of marine toxins, peptides, alkaloids, nucleosides and prostanoids are discussed in detail. Biological, toxicological and clinical evaluations are also dealt with to ensure that the book may be adopted at any stage by any practicing organic chemist or biologist, working in academia or in R and D divisions of pharmaceutical companies. Each chapter in the book includes an abstract to highlight the major points discussed in the text and concluding remarks are given. References to books, monographs, review articles and original papers are provided at the end of each chapter.
Author :
Publisher : Elsevier
ISBN 13 : 0080453821
Total Pages : 7944 pages
Book Rating : 4.0/5 (84 download)
Download or read book Comprehensive Natural Products II written by and published by Elsevier. This book was released on 2010-03-05 with total page 7944 pages. Available in PDF, EPUB and Kindle. Book excerpt: This work presents a definitive interpretation of the current status of and future trends in natural products—a dynamic field at the intersection of chemistry and biology concerned with isolation, identification, structure elucidation, and chemical characteristics of naturally occurring compounds such as pheromones, carbohydrates, nucleic acids, and enzymes. With more than 1,800 color figures, Comprehensive Natural Products II features 100% new material and complements rather than replaces the original work (©1999). Reviews the accumulated efforts of chemical and biological research to understand living organisms and their distinctive effects on health and medicine Stimulates new ideas among the established natural products research community—which includes chemists, biochemists, biologists, botanists, and pharmacologists Informs and inspires students and newcomers to the field with accessible content in a range of delivery formats Includes 100% new content, with more than 6,000 figures (1/3 of these in color) and 40,000 references to the primary literature, for a thorough examination of the field Highlights new research and innovations concerning living organisms and their distinctive role in our understanding and improvement of human health, genomics, ecology/environment, and more Adds to the rich body of work that is the first edition, which will be available for the first time in a convenient online format giving researchers complete access to authoritative Natural Products content
Author : Feng Geng
Publisher :
ISBN 13 :
Total Pages : 436 pages
Book Rating : 4.3/5 (129 download)
Download or read book Synthetic & Mechanistic Investigations of the Wittig Rearrangements and Synthetic Studies Toward Amphidinolide A written by Feng Geng and published by . This book was released on 2001 with total page 436 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Liesl Marsh
Publisher :
ISBN 13 :
Total Pages : 242 pages
Book Rating : 4.:/5 (156 download)
Download or read book Synthetic Studies on Marine Natural Products written by Liesl Marsh and published by . This book was released on 2005 with total page 242 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Download or read book Synthesis of Biologically Active Marine Natural Product Analogues written by and published by . This book was released on 2006 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: Natural products have long been a source of inspiration for many drugs in human use. The Andersen lab examines compounds from marine sources that can be used as lead structures for drug discovery. Synthetic studies, structure-activity relationships (SAR) and biological findings of two such compounds are described in this thesis. The first is pelorol, a meroterpene isolated from a tropical sponge Dactylospongia elegans. Pelorol is a small molecule activator of SHIP 1, a phosphatase that is a negative regulator of the P13K pathway in hematopoetic cells. Using a synthetic route from a previous co-worker, Lu Yang, a series of SHIP 1 activating compounds based on pelorol were synthesized. These compounds were evaluated for selectivity, potency, and efficacy in a series of biological studies, leading to the discovery of 2.27 as a preclinical lead compound. Water-soluble prodrugs of the SHIP 1-activating compounds were also synthesized and their properties reported. The second compound examined is ceratamine A, an alkaloid isolated from the sponge Pseudoceratina sp. from Papua New Guinea. Ceratamines A and B are microtubule stabilizing antimitotic agents that may be useful in cancer chemotherapy. The core imidazo[4,5,d]azepine heterocycle of the ceratamines has no precedent among known synthetic or natural compounds. The relatively simple structure of the ceratamines and the novel antimitotic phenotype they generate makes them attractive targets. Desbromo ceratamine A (3.44) was synthesized by an efficient and scaleable route, confirming the structure of ceratamine A and validating the biological activity of the core pharmacophore. Synthetic efforts towards ceratamine A were ultimately thwarted by the inability to install the bromine atoms present in the natural product. A significant finding is that the bromine atoms in ceratamine A contribute significantly to the antimitotic potency of the compound necessitating a bioisosteric approach to more potent antimitotic ceratami.
