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Studies Directed Toward The Synthesis Of The B Type Amphidinolide Natural Products Using Nickel Catalyzed Reductive Couplings Of Enynes And Carbonyl Compounds
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Book Synopsis Studies Directed Toward the Synthesis of the B-type Amphidinolide Natural Products Using Nickel-catalyzed Reductive Couplings of Enynes and Carbonyl Compounds by : Andrew Michael Lauer
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].
Book Synopsis Diastereoselective Nickel-catalyzed Reductive Coupling of Alkynes and Aldehydes and Application Towards the B-type Amphidinolides by : Chudi O. Ndubaku
Download or read book Diastereoselective Nickel-catalyzed Reductive Coupling of Alkynes and Aldehydes and Application Towards the B-type Amphidinolides written by Chudi O. Ndubaku and published by . This book was released on 2006 with total page 482 pages. Available in PDF, EPUB and Kindle. Book excerpt: The application of recently developed stereoselective nickel-catalyzed reductive coupling reactions of alkynes and aldehydes to the synthesis of complex natural product targets was explored. The "B-Type" amphidinolides were selected as ideal targets owing to their molecular complexity and the paucity of synthetically viable means for their total construction. The diastereoselective nickel-catalyzed reductive coupling of simple aryl-substituted alkynes and a-oxyaldehydes was developed and applied to the construction of the C15-C26 region of amphidinolide H3. ... Alternatively, the nickel-catalyzed reductive coupling reaction of 1,3-enynes and aldehydes was found to be a very effective way of installing the congested 1,3-diene moiety common to all members of this class of natural products. This methodology was further examined as a fragment coupling strategy for the syntheses of amphidinolides G3 and H4. This allowed for a highly convergent and functional group tolerant assembly of these ... molecules and, to date, stands as the most complicated setting for the application of the catalytic reductive coupling reaction.
Book Synopsis Dissertation Abstracts International by :
Download or read book Dissertation Abstracts International written by and published by . This book was released on 2007 with total page 902 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis I. Enantioselective Nickel-catalyzed Reductive Coupling Reactions of Alkynes and Aldehydes by : Elizabeth Anne Colby Davie
Download or read book I. Enantioselective Nickel-catalyzed Reductive Coupling Reactions of Alkynes and Aldehydes written by Elizabeth Anne Colby Davie and published by . This book was released on 2005 with total page 332 pages. Available in PDF, EPUB and Kindle. Book excerpt: (Cont.) A model for the stereoselectivity observed in the macrocyclizations is also proposed. ... amphidinolide T1 amphidinolide T4 * site of catalytic, stereoselective macrocyclization.
Book Synopsis Nickel-catalyzed Reductive Coupling Reactions by : Katrina Sue Woodin
Download or read book Nickel-catalyzed Reductive Coupling Reactions written by Katrina Sue Woodin and published by . This book was released on 2007 with total page 157 pages. Available in PDF, EPUB and Kindle. Book excerpt: Catalytic Asymmetric Reductive Coupling of 1,3-Enynes and Aromatic Aldehydes Nickel-catalyzed reductive coupling reactions of 1,3-enynes and aromatic aldehydes efficiently afford conjugated dienols in excellent regioselectivity and modest enantioselectivity. These reactions were conducted in the presence of a catalytic ligand (R)-ferrocenyl(2-isopropylphenyl)phenylphosphine, whose overall synthesis was improved during the course of this investigation. 1-(Trimethylsilyl)-substituted enynes are shown to be efficient coupling partners in these reactions, and the dienol products formed readily undergo protiodesilylation under mild conditions. ... Catalytic, Asymmetric, Intramolecular Reductive Coupling of 1,1-Disubstituted Epoxides and Alkynes: Total Synthesis of Pumiliotoxin 209F and 251D Pumiliotoxins 209F and 251 D were prepared using a novel nickel-catalyzed intramolecular cyclizations between alkynes and 1,1-disubstituted epoxides. These cyclizations formed exclusively endo products without the use of a directing group on the alkyne. The synthesis of the reductive coupling precursors involved a diastereoselective sulfur ylide epoxidation of a proline-derived methyl ketone, where the choice of sulfonium salt conferred a major effect on the diastereoselectivity.
Book Synopsis Studies Toward the Synthesis of Amphidinolide B1 and the B-type Amphidinolides by : Hugo M. Eng
Download or read book Studies Toward the Synthesis of Amphidinolide B1 and the B-type Amphidinolides written by Hugo M. Eng and published by . This book was released on 1998 with total page 240 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Directory of Graduate Research by : American Chemical Society. Committee on Professional Training
Download or read book Directory of Graduate Research written by American Chemical Society. Committee on Professional Training and published by . This book was released on 2005 with total page 1932 pages. Available in PDF, EPUB and Kindle. Book excerpt: Faculties, publications and doctoral theses in departments or divisions of chemistry, chemical engineering, biochemistry and pharmaceutical and/or medicinal chemistry at universities in the United States and Canada.
Book Synopsis Studies Toward the Synthesis of the Amphidinolides by : Brian J. Myers
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:
Book Synopsis Total Synthesis of Welwitindolinones and Nickel-Catalyzed Reactions of Amide Derivatives by : Nicholas Anthony Weires
Download or read book Total Synthesis of Welwitindolinones and Nickel-Catalyzed Reactions of Amide Derivatives written by Nicholas Anthony Weires and published by . This book was released on 2017 with total page 560 pages. Available in PDF, EPUB and Kindle. Book excerpt: This dissertation describes our efforts toward the total synthesis of welwitindolinone natural products, as well as the development of reactions involving the nickel-catalyzed activation of amide C-N bonds. The welwitindolinones have been long-standing targets in total synthesis for over two decades, and this dissertation describes two completed total syntheses of these alkaloids. In addition, several nickel-catalyzed transformations of amides are outlined, each of which demonstrate the powerful reactivity of nickel and highlight the utility of amides as synthetic building blocks. Chapters one and two present our enantiospecific total syntheses of the welwitindolinone alkaloids N-methylwelwitindolinone D isonitrile and N-methylwelwitindolinone B isothiocyanate. Our approach to these natural products features an aryne cyclization to construct the bicyclo[4.3.1]decane core of the molecules, as well as a C-H nitrene insertion reaction to introduce the bridgehead nitrogen substituent. In chapter one, a dual C-H functionalization event installs the challenging ether linkage and allows for completion of (-)-N-methylwelwitindolinone D isonitrile. In chapter two, a regio- and diastereoselective chlorinative oxabicyclic opening is detailed, which enables the first total synthesis of N-methylwelwitindolinone B isothiocyanate. Chapters three, four, and five describe the development of nickel-catalyzed carbon-carbon bond-forming reactions of amides. More specifically, chapters three and four outline the Suzuki-Miyaura couplings of aromatic and aliphatic amides, respectively, whereas chapter five details the alkylation of amide derivatives. These methodologies represent mild and complementary tools to the Weinreb ketone synthesis, proceeding through the nickel-catalyzed activation of the amide C-N bond. It is shown that amides, which were traditionally thought of as inert functionalities, can be utilized as synthons in C-C bond-forming reactions. Chapter six describes a method for the benchtop delivery of Ni(cod)2 involving the encapsulation of Ni(cod)2 in paraffin wax. Due to air- and moisture-sensitivity, Ni(cod)2 is normally handled under an inert atmosphere. Using our method of wax encapsulation, several nickel-catalyzed transformations are performed without the use of a glove box, including various amide C-N bond cleavage reactions. These studies are aimed at promoting the widespread use of nickel in transition metal catalysis. Chapter seven illustrates the kinetic modeling of the nickel-catalyzed esterification of amides. By developing a kinetic model, an optimization is undertaken that allows for the employment of catalyst loadings as low as 0.4 mol% nickel. This demonstration is intended to foster the advancement of kinetic modeling as a powerful tool in methodology development.
Book Synopsis Journal by : American Chemical Society
Download or read book Journal written by American Chemical Society and published by . This book was released on 2004 with total page 1042 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Toward the Total Synthesis of Amphidinolide C by : Robert H. Bates
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.
Book Synopsis Nickel-catalyzed Reductive Coupling of Alkyl, Allyl and Vinyl Electrophiles by : Michael R. Prinsell
Download or read book Nickel-catalyzed Reductive Coupling of Alkyl, Allyl and Vinyl Electrophiles written by Michael R. Prinsell and published by . This book was released on 2013 with total page 187 pages. Available in PDF, EPUB and Kindle. Book excerpt: "The nickel-catalyzed reductive coupling of two organic electrophiles to form new carbon-carbon bonds is a fast emerging field of chemistry, with applications to the synthesis of medicinally interesting compounds. This method is an alternative to traditional transition metal-catalyzed cross-coupling reactions of organic electrophiles with organometallic nucleophiles. This thesis details the author's work towards the development of several reactions to reductively couple organic molecules to form Csp3-Csp3 bonds, including alkyl, allyl and vinyl halides. Chapter 1 delves into the background of traditional metal-catalyzed crosscoupling reactions as well as the advantages and challenges associated with using a reductive method to construct C-C bonds. In particular this chapter presents the specific challenges associated with the formation of a carbon-carbon bond between two Csp3 hybridized carbons. Chapter 2 outlines the development of a mild, general dimerization reaction of alkyl halides. This chapter also focuses on the use of sodium iodide to extend the coupling to molecules that are unreactive to the standard reaction conditions. Chapter 3 details work towards the cross-coupling of two alkyl halides. While cross-selectivity remains a challenge, some potential solutions are discussed. Chapter 4 presents the optimization and reaction scope of the coupling of allyl acetates with secondary alkyl halides, as well as progress towards couplings with primary alkyl halides. In addition, the first report of the catalytic coupling of vinyl bromides with allyl acetates is reported. Chapter 5 focuses on work towards the reductive cyclization of alkyl halides and allyl acetates. Initial results show promising diastereomeric ratios. Chapter 6 details work on the dehydrogenative synthesis of bipyridine and terpyridine ligands. These ligands are useful and are used for many reductive coupling reactions in the Weix group"--Pages vi.
Book Synopsis Stereoselective Alkene Synthesis by : Jianbo Wang
Download or read book Stereoselective Alkene Synthesis written by Jianbo Wang and published by Springer. This book was released on 2012-08-13 with total page 283 pages. Available in PDF, EPUB and Kindle. Book excerpt: Stereoselective Synthesis of Tetrasubstituted Alkenes via Torquoselectivity-Controlled Olefination of Carbonyl Compounds with Ynolates, by Mitsuru Shindo and Kenji Matsumoto.- Stereoselective Synthesis of Z-Alkenes, by Woon-Yew Siau, Yao Zhang and Yu Zhao.- Stereoselective Synthesis of Mono-fluoroalkenes, by Shoji Hara.- Recent Advances in Stereoselective Synthesis of 1,3-Dienes, by Michael De Paolis, Isabelle Chataigner and Jacques Maddaluno.- Selective Olefination of Carbonyl Compounds via Metal-Catalyzed Carbene Transfer from Diazo Reagents, by Yang Hu and X. Peter Zhang.- Selective Alkene Metathesis in the Total Synthesis of Complex Natural Product, by Xiaoguang Lei and Houhua Li.- Olefination Reactions of Phosphorus-Stabilized Carbon Nucleophiles, by Yonghong Gu and Shi-Kai Tian.- Alkene Synthesis Through Transition Metal-Catalyzed Cross-Coupling of N-Tosylhydrazones, by Yan Zhang and Jianbo Wang.
Book Synopsis Applied Cross-Coupling Reactions by : Yasushi Nishihara
Download or read book Applied Cross-Coupling Reactions written by Yasushi Nishihara and published by Springer Science & Business Media. This book was released on 2012-12-14 with total page 247 pages. Available in PDF, EPUB and Kindle. Book excerpt: “Applied Cross-Coupling Reactions” provides students and teachers of advanced organic chemistry with an overview of the history, mechanisms and applications of cross-coupling reactions. Since the discovery of the transition-metal-catalyzed cross-coupling reactions in 1972, numerous synthetic uses and industrial applications have been developed. The mechanistic studies of the cross-coupling reactions have disclosed that three fundamental reactions: oxidative addition, transmetalation, and reductive elimination, are involved in a catalytic cycle. Cross-coupling reactions have allowed us to produce a variety of compounds for industrial purposes, such as natural products, pharmaceuticals, liquid crystals and conjugate polymers for use in electronic devices. Indeed, the Nobel Prize for Chemistry in 2010 was awarded for work on cross-coupling reactions. In this book, the recent trends in cross-coupling reactions are also introduced from the point of view of synthesis design and catalytic activities of transition-metal catalysts.
Book Synopsis Synthetic Studies Toward the Total Synthesis of the Hydrophobic Domain of the Amphidinolide B-type Isomers by : Hugo M. Eng
Download or read book Synthetic Studies Toward the Total Synthesis of the Hydrophobic Domain of the Amphidinolide B-type Isomers written by Hugo M. Eng and published by . This book was released on 1994 with total page 134 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Studies Directed Toward the Total Synthesis of Batzelladine A by : Ewa Fredette
Download or read book Studies Directed Toward the Total Synthesis of Batzelladine A written by Ewa Fredette and published by . This book was released on 2002 with total page 136 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Book Synopsis Synthetic Studies Towards Galbonolide B. by : Peter Thomson
Download or read book Synthetic Studies Towards Galbonolide B. written by Peter Thomson and published by . This book was released on 1999 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
