Download or read book Towards the Total Synthesis of Amphidinolide T Family written by Flavien Labre and published by . This book was released on 2012 with total page 233 pages. Available in PDF, EPUB and Kindle. Book excerpt: Amphidinolides T are challenging natural targets for the total synthesis community because of their unique structural architecture. This thesis describes the investigations of the establishment of a novel and convenient route to synthesise four members of the natural product family, amphidinolides T1 and T3-5, from a common late-stage intermediate. The key transformations towards the synthetic pathway are ring formation reactions. The trans-tetrahydrofuran ring is forged efficiently via diastereoselective [2,3]-sigmatropic rearrangement of an oxonium ylide from diazo-generated metal carbenoids. Coupling of a side chain is achieved using a sequence of esterification and RCM reactions. Alternatively, a one-pot RCM followed by hydrogenation is described to shorten the synthetic route.

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:

Download or read book Towards the Total Synthesis of Amphidinolide F written by Daniel A. Mills and published by . This book was released on 2021 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:

Download or read book Progress Towards the Total Synthesis of Amphidinolide E written by Andrew Frederick Nolting and published by . This book was released on 2006 with total page 194 pages. Available in PDF, EPUB and Kindle. Book excerpt:

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.

Download or read book Total Synthesis of Members of the Amphidinolide Family of Natural Products written by Filippo Romiti and published by . This book was released on 2015 with total page 226 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Download or read book Towards the Total Synthesis of Amphidinolide C written by Guang Yang and published by . This book was released on 2013 with total page 213 pages. Available in PDF, EPUB and Kindle. Book excerpt:

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:

Download or read book Progress Towards the Total Synthesis of the Potent Antitumor Antibiotic Amphidinolide C written by Jesse D. Carrick and published by . This book was released on 2004 with total page 170 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Download or read book The Total Synthesis of the Assigned Structure of Amphidinolide A written by Lamont R. Terrell and published by . This book was released on 2002 with total page 530 pages. Available in PDF, EPUB and Kindle. Book excerpt:

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:

Download or read book Progress Towards the Total Synthesis of Amphidinolide C written by Nicholas A. Morra and published by . This book was released on 2012 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt: A second generation catalyst for the Mukaiyama oxidative cyclization for the formation of trans-THF rings is described. Co(nmp)2, displays increased stability to the reaction conditions, resulting in lower catalyst loadings, lower reaction temperatures, and significantly higher purity and yields of the products. Three procedures have been developed with this new water-soluble catalyst that greatly simplifies the post-reaction purification, making this procedure the premier method of forming trans-THF rings. This new catalyst has been applied towards the total synthesis of the potently bioactive macrocycle, Amphidinolide C. Herein we report the successful synthesis of several fragments of the natural product, and our attempts at coupling them to complete the synthesis. The C(1)-C(9) was achieved via two routes, both utilizing the highly effective oxidation catalyst Co(nmp)2 to form the methyl substituted trans-THF ring. Synthetic highlights include a regioselective Shi epoxidation, and the design and introduction of a novel Lewis acid (BF2OBn×OEt2) to facilitate a stereoselective reductive epoxide opening. The C(18)-C(34) fragment was also achieved via two routes, culminating in both the shortest (11 steps) and highest yielding (26% overall yield) approaches to this segment. Synthetic highlights of this fragment include a selective methylation of a diyne, and a highly selective alkynylation of a THF aldehyde, achieving excellent dr (>20:1) without the addition of an external chiral compound. Advanced intermediates comprising the entirety of the carbon backbone of the molecule have been synthesized, which in theory could complete the total synthesis in as few as two bond forming steps.

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:

Download or read book The Total Synthesis of the Proposed Structure of Amphidinolide A written by Joseph Samuel Ward and published by . This book was released on 2002 with total page 396 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Download or read book Towards a Total Synthesis of amphidinolide K written by Natalie E. Campbell and published by . This book was released on 2014 with total page pages. Available in PDF, EPUB and Kindle. Book excerpt:

Download or read book Progress Towards the Total Synthesis and Structural Assignment of Amphidinolide N and Caribenolide I written by William E. Brenzovich (Jr.) and published by . This book was released on 2008 with total page 916 pages. Available in PDF, EPUB and Kindle. Book excerpt:

Download or read book Strategies and Tactics in Organic Synthesis written by Michael Harmata and published by Academic Press. This book was released on 2004-11-03 with total page 522 pages. Available in PDF, EPUB and Kindle. Book excerpt: This title provides a forum for investigators to discuss their approach to the science and art of organic synthesis in a unique way. There are stories that vividly demonstrate the power of the human endeavour known as organic synthesis and the creativity and tenacity of its practitioners.