Studies Toward The Total Synthesis Of Norzoanthamine
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Author |
: Mark Robert Herbert |
Publisher |
: |
Total Pages |
: 260 |
Release |
: 2004 |
ISBN-10 |
: IND:30000094862210 |
ISBN-13 |
: |
Rating |
: 4/5 (10 Downloads) |
Synopsis Studies Toward the Total Synthesis of Norzoanthamine by : Mark Robert Herbert
Author |
: Haoran Xue |
Publisher |
: |
Total Pages |
: |
Release |
: 2013 |
ISBN-10 |
: OCLC:869384797 |
ISBN-13 |
: |
Rating |
: 4/5 (97 Downloads) |
Synopsis Toward the Total Synthesis of Norzoanthamine: The Development of a Transannular Michael Reaction Cascade by : Haoran Xue
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 |
: |
Total Pages |
: 380 |
Release |
: 2000 |
ISBN-10 |
: IND:30000067782965 |
ISBN-13 |
: |
Rating |
: 4/5 (65 Downloads) |
Synopsis Part I: Studies Towards the Total Synthesis of Zoanthamine Alkaloids Part II: Total Synthesis of (-)-lankacyclinol by : Guillermo Stanley Cortez Veliz
Author |
: Miguel A. Sierra |
Publisher |
: John Wiley & Sons |
Total Pages |
: 297 |
Release |
: 2013-07-11 |
ISBN-10 |
: 9783527654642 |
ISBN-13 |
: 352765464X |
Rating |
: 4/5 (42 Downloads) |
Synopsis More Dead Ends and Detours by : Miguel A. Sierra
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 |
: |
Total Pages |
: 532 |
Release |
: 2003 |
ISBN-10 |
: IND:30000082018304 |
ISBN-13 |
: |
Rating |
: 4/5 (04 Downloads) |
Synopsis Part I. Total Synthesis of (-)-ratjadone Part II. Studies Toward the Total Synthesis of Zoanthenol by : David C. Ihle
Author |
: Amir Sabahi |
Publisher |
: |
Total Pages |
: 536 |
Release |
: 2007 |
ISBN-10 |
: OCLC:190790173 |
ISBN-13 |
: |
Rating |
: 4/5 (73 Downloads) |
Synopsis Studies Toward the Total Synthesis of Dihydroflustramine C and Perophoramidine by : Amir Sabahi
Author |
: Jone Iriondo-Alberdi |
Publisher |
: |
Total Pages |
: 232 |
Release |
: 2007 |
ISBN-10 |
: OCLC:646744683 |
ISBN-13 |
: |
Rating |
: 4/5 (83 Downloads) |
Synopsis Studies Towards the Total Synthesis of Merrilactone A by : Jone Iriondo-Alberdi
Author |
: Induka Ruwanthi Abeysena |
Publisher |
: |
Total Pages |
: |
Release |
: 2004 |
ISBN-10 |
: OCLC:1101259159 |
ISBN-13 |
: |
Rating |
: 4/5 (59 Downloads) |
Synopsis Studies Towards the Total Synthesis of Nitramine and Agelastatin by : Induka Ruwanthi Abeysena
Author |
: Zhaoyang Meng |
Publisher |
: |
Total Pages |
: 268 |
Release |
: 2006 |
ISBN-10 |
: OCLC:74207537 |
ISBN-13 |
: |
Rating |
: 4/5 (37 Downloads) |
Synopsis Asymmetric Synthesis of Merrilactone A ; Studies Toward the Total Synthesis of Pinnamine by : Zhaoyang Meng
Author |
: Karsten Meyer |
Publisher |
: |
Total Pages |
: 0 |
Release |
: 2009 |
ISBN-10 |
: OCLC:643637251 |
ISBN-13 |
: |
Rating |
: 4/5 (51 Downloads) |
Synopsis Studies Towards the Total Synthesis of Merrilactone A by : Karsten Meyer