Author: Darren HarveyPublisher:
ISBN:
Category :
Languages : en
Pages :
Book Description
Studies Towards the Total Synthesis of Novel Opiate and Amaryllidaceae Alkaloids
Author: Darren HarveyStudies Directed Towards the Total Synthesis of Certain Amaryllidaceae Alkaloids
Author: Cameron J. CowdenPublisher:
ISBN:
Category : Alkaloids
Languages : en
Pages : 440
Book Description
The Total Synthesis of (")-morphine and ( - )-galanthamine
Author: Neeraj Prakash SanePublisher:
ISBN:
Category :
Languages : en
Pages : 420
Book Description
The opiate alkaloid ( - )-morphine and the Amaryllidaceae alkaloid ( - )-galanthamine are well known for their analgesic and anticholinergic properties, respectively. The chemical feature that connects these two molecules is that they are both biosynthesized from an ortho-para phenolic oxidative coupling. Attempts to mimic this aesthetic chemistry in the laboratory for the practical production of these alkaloids have not resulted in good yields of these compounds and there is a lot of scope for improvement. Despite the enormous amount of work devoted to this area, the simple para-alkylation of an appropriately substituted phenol derivative to generate a cross conjugated 2, 5-cyclohexadienone has not been reported. This strategy would avoid the low-yielding phenolic oxidation reaction and the product would merely require a double reductive amination of the aromatic aldehyde and the latent aldehyde (in the acetal) to produce narwedine, the synthetic precursor to ( - )-galanthamine. On the other hand, the same intermediate can be elaborated to (")-morphine via a Henry reaction, followed by reduction and reductive amination. Following the aforementioned methodology, we have successfully completed the synthesis of both these alkaloids via the common intermediate, a 2, 5-cross-conjugated cyclohexadienone. A demonstration of the use of this methodology towards achieving an enantioselective synthesis of these compounds has also been made. The overall yield of the 8 step procedure for galanthamine proceeds in 65% yield, which is approximately five times the yield of the current manufacturing process for this molecule. The synthesis of (")-morphine, for the first time, allows access to codeine without having to reduce codeinone and, with an overall yield of 20% for the 14 step process, makes this the shortest synthesis of morphine.
Total Synthesis of Amaryllidaceae Alkaloids of the 5,11-methanomorphanthridine Type
Author: Jaechul ShimPart I. General Approach to the Total Synthesis of 9-methoxy Substituted Indole Alkaloids
Author: Jun MaPublisher:
ISBN:
Category : Antimalarials
Languages : en
Pages : 464
Book Description
Mineral Studies, Dedicated to Paul Francis Kerr
Author: Index to Theses with Abstracts Accepted for Higher Degrees by the Universities of Great Britain and Ireland and the Council for National Academic Awards
Author: Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 434
Book Description
Theses on any subject submitted by the academic libraries in the UK and Ireland.
From Biosynthesis to Total Synthesis
Author: Alexandros L. ZografosPublisher: John Wiley & Sons
ISBN: 1118753569
Category : Science
Languages : en
Pages : 584
Book Description
Focusing on biosynthesis, this book provides readers with approaches and methodologies for modern organic synthesis. By discussing major biosynthetic pathways and their chemical reactions, transformations, and natural products applications; it links biosynthetic mechanisms and more efficient total synthesis. • Describes four major biosynthetic pathways (acetate, mevalonate, shikimic acid, and mixed pathways and alkaloids) and their related mechanisms • Covers reactions, tactics, and strategies for chemical transformations, linking biosynthetic processes and total synthesis • Includes strategies for optimal synthetic plans and introduces a modern molecular approach to natural product synthesis and applications • Acts as a key reference for industry and academic readers looking to advance knowledge in classical total synthesis, organic synthesis, and future directions in the field
British National Bibliography for Report Literature
Author: Publisher:
ISBN:
Category : Dissertations, Academic
Languages : en
Pages : 718
Book Description
The Chemistry and Biology of Isoquinoline Alkaloids
Author: J.D. PhillipsonPublisher: Springer Science & Business Media
ISBN: 3642701280
Category : Science
Languages : en
Pages : 315
Book Description
Isoquinolines form one of the largest groups of plant alkaloids and they in clude a number of valuable clinical agents such as codeine, morphine, eme tine and tubocurarine. Research into different aspects of isoquinolines con tinues in profusion, attracting the talents of botanists, chemists, bioche mists, analysts, pharmacists and pharmacologists. Many of these aspects are of an interdisciplinary nature, and in April 1984, The Phytochemical Society of Europe arranged a 3-day symposium on The Chemistry and Bi ology of Isoquinoline Alkaloids in order to provide a forum for scientists of differing disciplines who are united by a common interest in this one class of natural product. Each chapter in this volume is based on a lecture given at this symposium. Attempts have been made to make the aims and objectives, experimental findings and conclusions reached, intelligible to scientists of differing backgrounds. The introductory chapter, which is mainly based on a historical discus sion, stresses that plants containing isoquinolines have proved to be both a boon and a curse to mankind. The Opium Poppy, Papaver somniferum, produces the medicinally used alkaloids morphine, codeine, noscapine and papaverine whilst it also continues to provide drugs of abuse, particularly morphine and its readily prepared O,O-diacetyl derivative, heroin. Numer ous other alkaloids have been isolated from other members of the Papaver acea, and a knowledge of their presence and distribution within the various species has proved a useful adjunct to systematic botanical studies.