Studies Toward the Total Synthesis of Norzoanthamine PDF Download
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Author: Mark Robert Herbert
Publisher:
ISBN:
Category :
Languages : en
Pages : 260
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Author: Mark Robert Herbert
Publisher:
ISBN:
Category :
Languages : en
Pages : 260
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Author: Fatima R. Rivas
Publisher:
ISBN:
Category :
Languages : en
Pages : 499
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The work presented herein is the conclusion of synthetic studies toward the total synthesis of norzoanthamine. This dissertation on the norzoanthamine synthetic studies will be divided into 3 sections: (1) an introduction describing the norzoanthamine family along with their biological significance and previous studies; (2) a stereoselective synthesis of the ABC ring system, and the crucial development of the fully functionalized C ring; (3) a biomimetic approach towards norzoanthamine; which will discuss studies to create the C ring from a polyene system through a Diels-Alder reaction, studies to synthesize the A ring through a sigmatropic rearrangement, studies to generate the BC ring through an intramolecular Diels-Alder reaction from carvone as a chiral pool, development of isocarvone, and studies of 2-acylamino 1,3 dienes as a viable synthon to form the BC ring through a [4+2] cycloaddition reaction.
Author: Haoran Xue
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Category :
Languages : en
Pages :
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Norzoanthamine is a complex heptacyclic marine alkaloid isolated from colonial zoanthids. It potently inhibits loss of bone weight and strength in a postmenopausal osteoporosis mouse model, but its mode-of-action remains unknown. The scarcity of this natural product from its natural source and the need to access analogs for structure-activity relationship (SAR) study make it necessary to chemically synthesize this compound. However, the complex molecular skeleton, especially the highly functionalized and stereochemically complex ABC core structure of the natural product poses a significant challenge. As part of our efforts to develop a practical synthetic route to norzoanthamine, we systematically explored a transannular Michael reaction cascade in the context of the synthesis of angular 6-6-6 tricyclic ring system, a mimic of the ABC core structure of norzoanthamine. Using 1,7-bis-enones in the form of 14-membered macrocyclic lactone as model substrates, we demonstrated that both E,Z- and E,E-macrocycles underwent facile transannular reactions to give cis-syn-cis and trans-anti-trans ring systems, respectively. However, Z,E- and Z,Z- macrocycles did not cyclize under similar reactions. The similarities and differences between transannular Diels-Alder reactions and this transannular cyclization process were also disclosed. Building upon these preliminary studies, we developed a 12-linear step synthesis of the ABC carbocyclic core of norzoanthamine. It features an organocatalytic asymmetric intramolecular aldolization to set the stereochemistry of the entire molecule, a fragment coupling based on selective alkylation of a bis-enolate, and a transannular Michael reaction cascade for rapid and stereoselective synthesis of the polycyclic core. Subsequent Claisen rearrangement enabled installation of a handle for introduction of the bottom piece to complete the total synthesis. Other efforts toward the total synthesis have also been discussed. The electronic version of this dissertation is accessible from http://hdl.handle.net/1969.1/149334
Author: Guillermo Stanley Cortez Veliz
Publisher:
ISBN:
Category :
Languages : en
Pages : 380
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Author: Miguel A. Sierra
Publisher: John Wiley & Sons
ISBN: 352765464X
Category : Science
Languages : en
Pages : 297
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Success comes in many forms and in synthesis it can be a failure that results in their ultimate successful solutions. This long-awaited sequel to "Dead Ends and Detours" retains the proven concept while featuring over 20 new case studies of failed strategies and their (successful) solutions in natural product total synthesis. Additionally, computational models are used to discuss the problem in much more detail and to provide readers with additional information not found in the primary literature. The topics range from classic synthetic reactions (e.g. Diels Alder reaction), metal-mediated coupling reactions, metathesis, and asymmetric catalysis to the importance of protecting and activating groups. This book will benefit not only graduate students in organic chemistry but also advanced researchers as they gain knowledge derived from the step-by-step analysis of mistakes made in the past and, thus be able to improve their own chemical reaction planning. With its coverage of the most commonly applied reaction types, the book perfectly complements its predecessor, which focuses on general aspects, such as reactivity and selectivity.
Author: David C. Ihle
Publisher:
ISBN:
Category :
Languages : en
Pages : 532
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Author: Amir Sabahi
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Category : Indole
Languages : en
Pages : 536
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Author: Jone Iriondo-Alberdi
Publisher:
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Category :
Languages : en
Pages : 232
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Author: Induka Ruwanthi Abeysena
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Category :
Languages : en
Pages :
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Author: Karsten Meyer
Publisher:
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Category :
Languages : en
Pages : 0
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