Studies Toward the Total Synthesis of ( )-Cortistatin J Via an Intramolecular (4 3) Cycloaddition

Studies Toward the Total Synthesis of ( )-Cortistatin J Via an Intramolecular (4 3) Cycloaddition PDF Author: Lok-Lok Liu
Publisher: Open Dissertation Press
ISBN: 9781361255155
Category :
Languages : en
Pages :

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Book Description
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

Studies Toward the Total Synthesis of ( )-Cortistatin J Via an Intramolecular (4 3) Cycloaddition

Studies Toward the Total Synthesis of ( )-Cortistatin J Via an Intramolecular (4 3) Cycloaddition PDF Author: Lok-Lok Liu
Publisher: Open Dissertation Press
ISBN: 9781361255155
Category :
Languages : en
Pages :

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Book Description
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

Studies Toward the Total Synthesis of (+)-cortistatin J Via an Intramolecular (4+3) Cycloaddition

Studies Toward the Total Synthesis of (+)-cortistatin J Via an Intramolecular (4+3) Cycloaddition PDF Author: Lok-lok Liu
Publisher:
ISBN:
Category : Organic compounds
Languages : en
Pages : 430

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Studies Directed Toward the Total Synthesis of Cortistatin A

Studies Directed Toward the Total Synthesis of Cortistatin A PDF Author: Ryan Andrew Littich
Publisher:
ISBN:
Category :
Languages : en
Pages : 374

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Book Description
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.

Synthetic Studies Towards the Total Synthesis of Cortistatin A Synthesis of the Pentacyclic Core of Citreamicin Μ and GA-ring Model Studies

Synthetic Studies Towards the Total Synthesis of Cortistatin A Synthesis of the Pentacyclic Core of Citreamicin Μ and GA-ring Model Studies PDF Author: Shawn Thomas Blumberg
Publisher:
ISBN:
Category :
Languages : en
Pages : 1130

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Book Description
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.

Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies Towards (+)-Cortistatin A

Part I. Total Synthesis and Structural Revision of (±)-Tricholomalides A and B. Part II. Synthetic Studies Towards (+)-Cortistatin A PDF Author: Zhang Wang
Publisher:
ISBN:
Category :
Languages : en
Pages :

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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.

Development of Methodologies Employing Rhodium Catalysis and Studies Toward the Total Synthesis of Cortistatin A

Development of Methodologies Employing Rhodium Catalysis and Studies Toward the Total Synthesis of Cortistatin A PDF Author: Anna Jane Smith (Ph. D.)
Publisher:
ISBN:
Category :
Languages : en
Pages : 602

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(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.

Studies of Transannular (4+3) Cycloadditions and Application to the Synthesis of (+)-cortistatin A

Studies of Transannular (4+3) Cycloadditions and Application to the Synthesis of (+)-cortistatin A PDF Author: 陳肇人
Publisher:
ISBN:
Category : Organic cyclic compounds
Languages : en
Pages : 0

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Studies Toward the Total Synthesis of Germacranolides Using [6[pi]+4[pi]] Chromium (0) Mediated Cycloaddition Reactions

Studies Toward the Total Synthesis of Germacranolides Using [6[pi]+4[pi]] Chromium (0) Mediated Cycloaddition Reactions PDF Author: Ilirian Dhimitruka
Publisher:
ISBN:
Category :
Languages : en
Pages : 132

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Part I. The Intramolecular Nitrile Oxide Cycloaddition Route to Spirocyclic Alkaloids. A Total Synthesis of Isonitramine and Sibirine

Part I. The Intramolecular Nitrile Oxide Cycloaddition Route to Spirocyclic Alkaloids. A Total Synthesis of Isonitramine and Sibirine PDF Author: Po-wai Yuen
Publisher:
ISBN:
Category : Organic compounds
Languages : en
Pages : 356

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Studies Directed Toward the Total Synthesis of (+)-jatrophone

Studies Directed Toward the Total Synthesis of (+)-jatrophone PDF Author: Gary J. Drtina
Publisher:
ISBN:
Category : Diterpenes
Languages : en
Pages : 314

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