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Studies Toward The Total Synthesis Of Cortistatin J Via An Intramolecular 4 3 Cycloaddition
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Book Synopsis Studies Toward the Total Synthesis of ( )-Cortistatin J Via an Intramolecular (4 3) Cycloaddition by : Lok-Lok Liu
Download or read book Studies Toward the Total Synthesis of ( )-Cortistatin J Via an Intramolecular (4 3) Cycloaddition written by Lok-Lok Liu and published by Open Dissertation Press. This book was released on 2017-01-26 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation, "Studies Toward the Total Synthesis of ( )-cortistatin J via an Intramolecular (4 3) Cycloaddition" by Lok-lok, Liu, 廖樂樂, was obtained from The University of Hong Kong (Pokfulam, Hong Kong) and is being sold pursuant to Creative Commons: Attribution 3.0 Hong Kong License. The content of this dissertation has not been altered in any way. We have altered the formatting in order to facilitate the ease of printing and reading of the dissertation. All rights not granted by the above license are retained by the author. DOI: 10.5353/th_b4659162 Subjects: Ring formation (Chemistry) Organic compounds - Synthesis
Book Synopsis Studies Toward the Total Synthesis of (+)-cortistatin J Via an Intramolecular (4+3) Cycloaddition by : Lok-lok Liu
Download or read book Studies Toward the Total Synthesis of (+)-cortistatin J Via an Intramolecular (4+3) Cycloaddition written by Lok-lok Liu and published by . This book was released on 2011 with total page 430 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Directed Toward the Total Synthesis of Cortistatin A by : Ryan Andrew Littich
Download or read book Studies Directed Toward the Total Synthesis of Cortistatin A written by Ryan Andrew Littich and published by . This book was released on 2010 with total page 374 pages. Available in PDF, EPUB and Kindle. Book excerpt: Studies directed toward the total synthesis of the cytotoxic steroidal alkaloid cortistatin A were carried out. In a model system, it was determined that a sequence of reactions involving a lithiocyclopropene addition-intramolecular [4 + 2] cycloaddition cascade and subsequent cyclopropylcarbinyl rearrangement allowed for ready access to the BCD rings of the core steroid. Implementation of this methodology en route to the fully functionalized natural product proved an effective means for the elaboration of the A ring carbocyclic framework.
Book Synopsis Synthetic Studies Towards the Total Synthesis of Cortistatin A Synthesis of the Pentacyclic Core of Citreamicin Μ and GA-ring Model Studies by : Shawn Thomas Blumberg
Download or read book Synthetic Studies Towards the Total Synthesis of Cortistatin A Synthesis of the Pentacyclic Core of Citreamicin Μ and GA-ring Model Studies written by Shawn Thomas Blumberg and published by . This book was released on 2016 with total page 1130 pages. Available in PDF, EPUB and Kindle. Book excerpt: The route to the key bicyclic intermediate was streamlined to eight steps in 16% yield, using a TMSI promoted coupling of a furan and an enone. Additionally, methodology for the selective ozonolysis of the bicyclic intermediate was developed via ozone titration. Work on the dihydroxylation step led to the discovery and development of a new pH-neutral Sharpless-style asymmetric dihydroxylation. The synthesis of pentacyclic core of citreamicin μ was accomplished in 12 steps. New methodologies were developed, including: an ortho- selective bromination of a vanillin derivative and the use of 4-(Phenylazo)diphenylamine (PDA) as an internal indicator for the acetylide coupling. The usefulness of PDA led to its development as a general all-purpose indicator for the titration of strong bases, Lewis acids and reducing agents. The discovery of (n-Bu)4NOAc as a privileged additive led to the development of new methods for the synthesis of isocoumarins and new methodology for the condensation of amino acids using LiMe4 was developed.
Book Synopsis Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies Towards (+)-Cortistatin A by : Zhang Wang
Download or read book Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies Towards (+)-Cortistatin A written by Zhang Wang and published by . This book was released on 2011 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: The first part describes the total synthesis and structural revision of (±)-tricholomalides A and B. The synthetic strategy started from a homo-Robinson annulation, followed by a ketene-olefin [2+2] cycloaddition to introduce the lactone ring. Then a Grignard-type reaction appended the isopropenyl moiety, and the synthesis of tricholomalides A and B was achieved. During the course of synthesis, the structures of tricholomalides A and B were revised. The second part describes the synthetic studies towards (+)-cortistatin A, especially the A ring functionalization. The C3 nitrogen was introduced by azide displacement, and C2 hydroxyl was built up by Luche reduction. The challenging C1 functionalization was achieved with bromine-induced methoxymethyl deprotection, and some interesting chemistry was found in this system. The synthetic endeavor set a promising stage for the total synthesis of cortistatin A.
Book Synopsis Development of Methodologies Employing Rhodium Catalysis and Studies Toward the Total Synthesis of Cortistatin A by : Anna Jane Smith (Ph. D.)
Download or read book Development of Methodologies Employing Rhodium Catalysis and Studies Toward the Total Synthesis of Cortistatin A written by Anna Jane Smith (Ph. D.) and published by . This book was released on 2009 with total page 602 pages. Available in PDF, EPUB and Kindle. Book excerpt: (Rh(CO)2Cl)2 has been shown to catalyze sequential, mechanistically-distinct transformations in one pot. Tandem allylic alkylation/cycloisomerization sequences have been developed to access valuable, complex structures from relatively simple substrates. A methodology for the enantioselective conjugate addition of 2-heteroaryl nucleophiles to a variety of Michael acceptors has been developed. This method was used successfully in an ongoing approach to the synthesis of cortistatin A. 10 linear steps have been completed towards the synthesis of cortistatin A, including a highly regioselective propargylation to install a quaternary carbon and a diastereoselective intramolecular Diels-Alder reaction.
Book Synopsis Studies of Transannular (4+3) Cycloadditions and Application to the Synthesis of (+)-cortistatin A by : 陳肇人
Download or read book Studies of Transannular (4+3) Cycloadditions and Application to the Synthesis of (+)-cortistatin A written by 陳肇人 and published by . This book was released on 2016 with total page 0 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Toward the Total Synthesis of Germacranolides Using [6[pi]+4[pi]] Chromium (0) Mediated Cycloaddition Reactions by : Ilirian Dhimitruka
Download or read book Studies Toward the Total Synthesis of Germacranolides Using [6[pi]+4[pi]] Chromium (0) Mediated Cycloaddition Reactions written by Ilirian Dhimitruka and published by . This book was released on 2000 with total page 132 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Part I. The Intramolecular Nitrile Oxide Cycloaddition Route to Spirocyclic Alkaloids. A Total Synthesis of Isonitramine and Sibirine by : Po-wai Yuen
Download or read book Part I. The Intramolecular Nitrile Oxide Cycloaddition Route to Spirocyclic Alkaloids. A Total Synthesis of Isonitramine and Sibirine written by Po-wai Yuen and published by . This book was released on 1987 with total page 356 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies in the Synthesis of Cyclopentanoid Natural Products by : James Michael Balkovec
Download or read book Studies in the Synthesis of Cyclopentanoid Natural Products written by James Michael Balkovec and published by . This book was released on 1985 with total page 440 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Toward the Total Synthesis of Jodrellin B and the Synthesis of Previously Inaccessible Bridehead Sultams by Radical and Anionic Intramolecular Cyclization by : Jeffrey D. Schloss
Download or read book Studies Toward the Total Synthesis of Jodrellin B and the Synthesis of Previously Inaccessible Bridehead Sultams by Radical and Anionic Intramolecular Cyclization written by Jeffrey D. Schloss and published by . This book was released on 2001 with total page 798 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Toward the Total Synthesis of Quartromicin by : Jun Qi
Download or read book Studies Toward the Total Synthesis of Quartromicin written by Jun Qi and published by . This book was released on 2006 with total page 114 pages. Available in PDF, EPUB and Kindle. Book excerpt: The quartromicins are a group of structurally complex macrocyclic natural products that display activity against herpes simplex virus type 1 (HSV-1), influenza, and HIV. The quartromicins contain four spirotetronate subunits (two endo and two exo spirotetronates) connected in an alternating head to tail manner. While previous synthetic studies in the Roush laboratory have led to the development of an efficient pathway to the endo spirotetronate subunits, the synthesis of the exo spirotetronate subunits has remained much more challenging.
Book Synopsis Studies on the Total Synthesis of Gambierol Via Endo-selective Epoxide-opening Cascades by : Tamara Halkina
Download or read book Studies on the Total Synthesis of Gambierol Via Endo-selective Epoxide-opening Cascades written by Tamara Halkina and published by . This book was released on 2016 with total page 367 pages. Available in PDF, EPUB and Kindle. Book excerpt: Progress towards the total synthesis of gambierol inspired by the biosynthetic hypothesis for ladder polyethers is described. Syntheses of the ABCD and FGH fragments have been completed in 29 and 3 1 steps, respectively, using water-promoted endo-selective epoxide-opening cascades to construct the poly-THP motifs. The concentration and temperature effects in the waterpromoted cascades were examined, and an operationally simple protocol was developed for the synthesis of polycyclic cascade products on multigram scale. [diagram] A sulfone tether between the ABCD and FGH fragments was used to facilitate an intramolecular olefination via the Ramberg-Backlund reaction. The highly site-selective hydrogenation of the fragment coupling alkene in the presence of H-ring alkene was developed using Noyori's hydrogenation catalyst, and several ring E cyclization precursors were subsequently prepared from C21 ketone. Investigation of a variety of methods for the C21-0 bond construction revealed a remarkably general spiroketalization pathway, which was previously unprecedented in ladder polyether synthesis and invariably led to the isolation of undesired 6,6-spiroketal products under most conditions. We have hypothesized that the presence of the FG ring junction methyl group disfavors the desired cyclization by exerting destabilizing 1,3-diaxial strain onto the newly forming ring junction of the requisite oxepane. We have therefore proposed that future studies examine the reverse direction for the synthesis of ring E via C16-0 bond formation. This approach would require installation of the tertiary alcohol on ring F prior to cyclization and would thus avoid the undesired reactivity resulting from the steric effects of the FG ring junction methyl group. [diagram]
Book Synopsis Studies Toward the Total Synthesis of ( - )-stolonidiol by : Thomas John Barton
Download or read book Studies Toward the Total Synthesis of ( - )-stolonidiol written by Thomas John Barton and published by . This book was released on 2012 with total page 362 pages. Available in PDF, EPUB and Kindle. Book excerpt: The marine diterpene ( - )-stolonidiol (1) has been shown to upregulate neuronal levels of acetylcholine. The mechanism through which a small molecule can impart this allosteric-like effect is currently unknown. A laboratory preparation of the natural product was undertaken in order to produce matieral for biological testing and elucidation of the unknown mechanism of action. During the course of this study, a tandem enyne-Suzuki reaction was investigated to form both rings of the fused bi-cyclic structure 26 in a single operation, but was met with undesired diastereoselectivity in the first cyclization step. The directing effect was found to be general on 1,6-homopropargyl enynes. Further efforts toward the molecule focused on an enantioselective formation of the cyclopentane core through an extension of a copper-mediated silylcyclization of epoxyalkyne 71. Using this intermediate two routes involving acrylate as a lynchpin to close the large ring were investigated. Additionally, a route designed to employ an intramolecular Knoevenagel condensation was explored to generate this ring system.
Book Synopsis Applications of the Intramolecular Schmidt Reaction Toward the Total Synthesis of (±)-Crinane by : Mendi Ann Morton
Download or read book Applications of the Intramolecular Schmidt Reaction Toward the Total Synthesis of (±)-Crinane written by Mendi Ann Morton and published by . This book was released on 1996 with total page 146 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Toward the Total Synthesis of Madindoline, and Interleukin-6 Inhibitor by : Shelley Kay Wolf
Download or read book Studies Toward the Total Synthesis of Madindoline, and Interleukin-6 Inhibitor written by Shelley Kay Wolf and published by . This book was released on 2000 with total page 80 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Application of the Type 2 Intramolecular Diels-Alder Reaction to Natural Product Synthesis: I. an Enantioselective Total Synthesis of (+)-adrenosterone ; II. Studies Toward the Synthesis of 9-deoxyphorbol by : Carolyn Diane Dzierba
Download or read book Application of the Type 2 Intramolecular Diels-Alder Reaction to Natural Product Synthesis: I. an Enantioselective Total Synthesis of (+)-adrenosterone ; II. Studies Toward the Synthesis of 9-deoxyphorbol written by Carolyn Diane Dzierba and published by . This book was released on 1997 with total page 298 pages. Available in PDF, EPUB and Kindle. Book excerpt:
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