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Author : Hugo M. Eng
Publisher :
ISBN 13 :
Total Pages : 240 pages
Book Rating : 4.:/5 (418 download)
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:
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 : Matthew A. Foster
Publisher :
ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (643 download)
Download or read book Studies Towards the Total Synthesis of Amphidinolides O and P written by Matthew A. Foster and published by . This book was released on 2001 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Yan Yu
Publisher :
ISBN 13 :
Total Pages : 52 pages
Book Rating : 4.:/5 (513 download)
Download or read book Studies Toward Total Synthesis of Amphidinolide A written by Yan Yu and published by . This book was released on 2001 with total page 52 pages. Available in PDF, EPUB and Kindle. Book excerpt:
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 : 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 : 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 : Jens-Martin Herold
Publisher :
ISBN 13 : 9781109044874
Total Pages : 324 pages
Book Rating : 4.0/5 (448 download)
Download or read book Toward a Total Synthesis of (+)-amphidinolide P and Related Studies written by Jens-Martin Herold and published by . This book was released on 2008 with total page 324 pages. Available in PDF, EPUB and Kindle. Book excerpt: Finally, novel palladium-catalyzed conjugate additions of organozinc reagents to alpha,beta-unsaturated aldehydes are discussed. This methodology can be diastereoselective and can be used for the selective preparation of (E)-silyl enol ethers. The palladium-catalyzed reaction is also compared to its copper-catalyzed counterpart.
Author : Andrew P. Osnowski
Publisher :
ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (87 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 pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Hugo M. Eng
Publisher :
ISBN 13 :
Total Pages : 134 pages
Book Rating : 4.:/5 (333 download)
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:
Author : Michael J. McCoy
Publisher :
ISBN 13 :
Total Pages : 198 pages
Book Rating : 4.3/5 ( download)
Download or read book Studies Toward the Total Syntheses of Amphidinolides C and F written by Michael J. McCoy and published by . This book was released on 2007 with total page 198 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.
Download or read book Towards the Synthesis of Amphidinolides C, F and U written by and published by . This book was released on 2008 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Ludovic Decultot
Publisher :
ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (16 download)
Download or read book Towards the Total Synthesis of Amphidinolides C and F. written by Ludovic Decultot and published by . This book was released on 2016 with total page 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 : Rex Everett Lidov
Publisher :
ISBN 13 :
Total Pages : pages
Book Rating : 4.:/5 (438 download)
Download or read book Studies Toward the Synthesis of 4-methyl-5,5-diethyluracil written by Rex Everett Lidov and published by . This book was released on 1936 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:
Author : Jin-Hyun Jeong
Publisher :
ISBN 13 :
Total Pages : 746 pages
Book Rating : 4.F/5 ( download)
Download or read book Studies Directed Toward the Synthesis of 2β-hydroxyjatrophone written by Jin-Hyun Jeong and published by . This book was released on 1993 with total page 746 pages. Available in PDF, EPUB and Kindle. Book excerpt:
