Author: Julien Genovino
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Studies Towards the Total Synthesis of (+)-spirastrellolide A.
Author: Julien Genovino
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Studies Toward the Total Synthesis of Spirastrellolide A
Author: Steven Merwin Kennedy
Publisher:
ISBN: 9781124149660
Category :
Languages : en
Pages : 242
Book Description
Chapter one of this dissertation describes background into the biological properties of spirastrellolide A (SA) as a potent and selective protein phosphatase inhibitor. It then goes on to provide information on the isolation, structural elucidation, and structural features of SA. Additionally, it compares SA to other natural products with similar biological activity. Finally, chapter one ends with a literature review of synthetic work on SA and the other known spirastrellolides. By highlighting the total syntheses of spirastrellolide A methyl ester by Paterson and spirastrellolide F methyl ester by Fürstner an overview of synthetic challenges, strategies, and methods is seen. Other synthetic progress on the spirastrellolides is also briefly acknowledged. Chapter two provides a detailed account of my spirastrellolide A synthetic progress. It begins by analyzing synthetic challenges inherent to SA. Then my hypothesized synthetic plan for a total synthesis of SA is outlined. Synthetic advancement toward specific fragments of the SA carbon chain is discussed. It covers strategies employed for building the carbon framework of the molecule while installing necessary stereocenters. As chapter two continues, studies toward the synthesis of four distinct fragments of SA are explored. A synthesis of the C41-C47 side chain is explained. The C33-C40 fragment synthesis is also described. Next, the synthesis of stereospecific chlorohydrin containing molecules is examined. Finally, the progress toward a synthesis of the C1-C16 fragment is described in detail. The synthesis of this fragment focuses partially on the incorporation of methodology previously developed in the Chamberlin laboratory to install a cis-tetrahydropyran ring and an anti-1,3-diol moiety. The chapter concludes with suggested work. Chapter three provides all of the necessary information and data to repeat the work reported in chapter two. It begins with experimental procedures for synthesizing each of the key intermediates mentioned in successful synthetic routes. Each experimental procedure is followed by experimental data. Finally, chapter three is followed by an appendix with 1H and 13C NMR spectra useful for identifying key molecular structures.
Publisher:
ISBN: 9781124149660
Category :
Languages : en
Pages : 242
Book Description
Chapter one of this dissertation describes background into the biological properties of spirastrellolide A (SA) as a potent and selective protein phosphatase inhibitor. It then goes on to provide information on the isolation, structural elucidation, and structural features of SA. Additionally, it compares SA to other natural products with similar biological activity. Finally, chapter one ends with a literature review of synthetic work on SA and the other known spirastrellolides. By highlighting the total syntheses of spirastrellolide A methyl ester by Paterson and spirastrellolide F methyl ester by Fürstner an overview of synthetic challenges, strategies, and methods is seen. Other synthetic progress on the spirastrellolides is also briefly acknowledged. Chapter two provides a detailed account of my spirastrellolide A synthetic progress. It begins by analyzing synthetic challenges inherent to SA. Then my hypothesized synthetic plan for a total synthesis of SA is outlined. Synthetic advancement toward specific fragments of the SA carbon chain is discussed. It covers strategies employed for building the carbon framework of the molecule while installing necessary stereocenters. As chapter two continues, studies toward the synthesis of four distinct fragments of SA are explored. A synthesis of the C41-C47 side chain is explained. The C33-C40 fragment synthesis is also described. Next, the synthesis of stereospecific chlorohydrin containing molecules is examined. Finally, the progress toward a synthesis of the C1-C16 fragment is described in detail. The synthesis of this fragment focuses partially on the incorporation of methodology previously developed in the Chamberlin laboratory to install a cis-tetrahydropyran ring and an anti-1,3-diol moiety. The chapter concludes with suggested work. Chapter three provides all of the necessary information and data to repeat the work reported in chapter two. It begins with experimental procedures for synthesizing each of the key intermediates mentioned in successful synthetic routes. Each experimental procedure is followed by experimental data. Finally, chapter three is followed by an appendix with 1H and 13C NMR spectra useful for identifying key molecular structures.
Synthetic Studies Toward the Total Synthesis of Sirodesmin A
Author: Daniel James Conatser
Publisher:
ISBN:
Category : Biosynthesis
Languages : en
Pages : 144
Book Description
Publisher:
ISBN:
Category : Biosynthesis
Languages : en
Pages : 144
Book Description
Towards the Total Synthesis of Spirastrellolide E
Author: Alexander Sokolsky
Publisher:
ISBN:
Category :
Languages : en
Pages : 698
Book Description
This dissertation describes progress towards the synthesis of spirastrellolide E, a potent cytotoxic marine macrolide. In particular, the synthesis of advanced southern hemisphere fragments is reported. Chapter 1 details the isolation, structural determination, and biological activity of the spirastrellolide family, as well as synthetic efforts towards members of the family. Chapter 2 describes the evolution of the Smith group synthetic strategy towards the spirastrellolides, details the choice of target for a total synthesis effort, and describes a successful first generation approach to a relevant advanced southern hemisphere fragment. Key steps involve a convergent Type I Anion Relay Chemistry (ARC) union and a gold catalyzed directed spiroketalization. Chapter 3 then revises the overall retrosynthetic analysis by proposing a novel strategy for hemisphere union, involving a cross metathesis/epoxidation/epoxide ring opening cascade, and describes the synthesis of more than 500 mg of a revised southern hemisphere fragment. In addition, the mechanism of the key directed gold catalyzed spiroketalization is discussed in detail. A stereochemical rationale for diverging outcomes during spiroketalization is described.
Publisher:
ISBN:
Category :
Languages : en
Pages : 698
Book Description
This dissertation describes progress towards the synthesis of spirastrellolide E, a potent cytotoxic marine macrolide. In particular, the synthesis of advanced southern hemisphere fragments is reported. Chapter 1 details the isolation, structural determination, and biological activity of the spirastrellolide family, as well as synthetic efforts towards members of the family. Chapter 2 describes the evolution of the Smith group synthetic strategy towards the spirastrellolides, details the choice of target for a total synthesis effort, and describes a successful first generation approach to a relevant advanced southern hemisphere fragment. Key steps involve a convergent Type I Anion Relay Chemistry (ARC) union and a gold catalyzed directed spiroketalization. Chapter 3 then revises the overall retrosynthetic analysis by proposing a novel strategy for hemisphere union, involving a cross metathesis/epoxidation/epoxide ring opening cascade, and describes the synthesis of more than 500 mg of a revised southern hemisphere fragment. In addition, the mechanism of the key directed gold catalyzed spiroketalization is discussed in detail. A stereochemical rationale for diverging outcomes during spiroketalization is described.
Studies Towards the Total Synthesis of Merrilactone A
Author: Jone Iriondo-Alberdi
Publisher:
ISBN:
Category :
Languages : en
Pages : 232
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages : 232
Book Description
Studies Towards the Total Synthesis of Merrilactone A
Author: Karsten Meyer
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages : 0
Book Description
Studies Toward the Total Synthesis of 8-O-methylsclerotiorinamine and 5-bromoochrephilone
Author: Daniel Mark Bruggemeyer
Publisher:
ISBN:
Category :
Languages : en
Pages : 104
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages : 104
Book Description
Studies Toward the Total Synthesis of Spiroketal Containing Natural Products: ( - )-talaromycin A and Averhectin B(1B)
Author: Rosemary O'Mahony
Publisher:
ISBN:
Category :
Languages : en
Pages : 167
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages : 167
Book Description
Total Synthesis of Spirastrellolide A Methyl Ester
Author: Jong Ho Lim
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
The Total Synthesis of (+)-spirastrellolide A Methyl Ester
Author: Philip James Maltas
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Publisher:
ISBN:
Category :
Languages : en
Pages :
Book Description