Formal Syntheses of Hirsutine and Rhynchophylline and Progress Toward the Enantioselective Total Synthesis of Citrinadin A PDF Download
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Author: Martin Youngjin Pettersson Publisher: ISBN: Category : Alkaloids Languages : en Pages : 714
Book Description
The diastereoselective formal syntheses of the corynanthe alkaloid hirsutine and oxindole alkaloid rhynchophylline are described. The general approach features the use of ring-closing metathesis (RCM) to construct an [alpha], [beta]-unsaturated lactam, which is subjected to 1,4-addition. The lithium enolate of ethyl-1,3-dithiolane-2-carboxylate was identified as the optimal nucleophile in these systems. A key feature of this approach is that the stereochemical outcome of the 1,4-addition can be effectively controlled by appropriately sequencing the indole Boc-protection step to give either the C(3)-H/C(15)-H cis or C(3)-H/C(15)-H trans stereochemical relationship. As a result, we have developed a unified approach to both the "normal" and "pseudo" corynanthe alkaloids. This finding was highlighted through the synthesis of the complete carbon skeleton of the archetypal normal corynanthe alkaloid dihydrocorynantheol. An efficient synthesis of the tricyclic spiroindolinone ABC-fragment of the marine alkaloid citrinadin A has been achieved. The synthesis relies on a novel asymmetric oxidative rearrangement of an indole to an oxindole using a chiral auxiliary on the indole nitrogen to achieve facial selectivity. The transformation proceeds via the epoxidation of the indole C(2), C(3) double bond using DMDO, followed by a silica gelmediated 1,2-epoxide rearrangement. Using this tactic, the spirooxindole of citrinadin A, which contains two adjacent quaternary centers, was formed in high yield and excellent diastereoselectivity. Efforts toward the fragment coupling of the tricyclic spiroindolinone with a 2,4,6-trisubstituted piperidine coupling partner are described.
Author: Martin Youngjin Pettersson Publisher: ISBN: Category : Alkaloids Languages : en Pages : 714
Book Description
The diastereoselective formal syntheses of the corynanthe alkaloid hirsutine and oxindole alkaloid rhynchophylline are described. The general approach features the use of ring-closing metathesis (RCM) to construct an [alpha], [beta]-unsaturated lactam, which is subjected to 1,4-addition. The lithium enolate of ethyl-1,3-dithiolane-2-carboxylate was identified as the optimal nucleophile in these systems. A key feature of this approach is that the stereochemical outcome of the 1,4-addition can be effectively controlled by appropriately sequencing the indole Boc-protection step to give either the C(3)-H/C(15)-H cis or C(3)-H/C(15)-H trans stereochemical relationship. As a result, we have developed a unified approach to both the "normal" and "pseudo" corynanthe alkaloids. This finding was highlighted through the synthesis of the complete carbon skeleton of the archetypal normal corynanthe alkaloid dihydrocorynantheol. An efficient synthesis of the tricyclic spiroindolinone ABC-fragment of the marine alkaloid citrinadin A has been achieved. The synthesis relies on a novel asymmetric oxidative rearrangement of an indole to an oxindole using a chiral auxiliary on the indole nitrogen to achieve facial selectivity. The transformation proceeds via the epoxidation of the indole C(2), C(3) double bond using DMDO, followed by a silica gelmediated 1,2-epoxide rearrangement. Using this tactic, the spirooxindole of citrinadin A, which contains two adjacent quaternary centers, was formed in high yield and excellent diastereoselectivity. Efforts toward the fragment coupling of the tricyclic spiroindolinone with a 2,4,6-trisubstituted piperidine coupling partner are described.
Author: John ApSimon Publisher: John Wiley & Sons ISBN: 0470129522 Category : Science Languages : en Pages : 579
Book Description
Each volume reviews the total synthesis of a set of compounds looking at syntheses reported historically and at the practice current at the time of publication. From volume 1 focusing on carbohydrates, prostagladins, nucleic acids, antibiotics, naturally occurring oxygen ring compounds and pyrrole pigments, the series continues with coverage of aromatic steroids, monoterpenes, triterpenes, sesquiterpenes, cannabinoids, natural inophores, insect pheromones and alkaloids. Volumes revisit the total synthesis of key compounds such as carbohydrates, nucleic acids and pyrrole pigments several times during the series building a picture of the historic development of total synthesis techniques for these major groups. Chapters are edited by experts in their field to give a complete overview of the best in the field at the time.
Author: John ApSimon Publisher: Wiley-Interscience ISBN: Category : Science Languages : en Pages : 582
Book Description
Each volume reviews the total synthesis of a set of compounds looking at syntheses reported historically and at the practice current at the time of publication. From volume 1 focusing on carbohydrates, prostagladins, nucleic acids, antibiotics, naturally occurring oxygen ring compounds and pyrrole pigments, the series continues with coverage of aromatic steroids, monoterpenes, triterpenes, sesquiterpenes, cannabinoids, natural inophores, insect pheromones and alkaloids. Volumes revisit the total synthesis of key compounds such as carbohydrates, nucleic acids and pyrrole pigments several times during the series building a picture of the historic development of total synthesis techniques for these major groups. Chapters are edited by experts in their field to give a complete overview of the best in the field at the time.
Author: Navjeet Kaur Publisher: Elsevier ISBN: 0443189420 Category : Science Languages : en Pages : 502
Book Description
5-Membered Heterocycle Synthesis Using Iodine presents both old and new methods for the synthesis of various five-membered heterocycles using iodine, providing information for making specific compounds using particular reagents. Heterocyclic frameworks represent the main structural subunits of many biologically active compounds and natural products, and the ability of heterocycles to act both as reactive pharmacophores and biomimetics has greatly contributed to their unique value as traditional key elements of various drugs. Contemporary developments in process chemistry and discovery emphasize novel sustainable synthetic pathways as fast and ecologically acceptable alternatives to the traditional protocols. This book serves as a guide for students, pharmacologists, biochemists, organic and medicinal chemists, researchers, and academic professionals to obtain easy access to synthetic protocols for different five-membered heterocycles using iodine. Covers the applications of five-membered heterocycles Highlights methodologies for the synthesis of five-membered heterocycles using iodine Contains the most up-to-date information in this fast-moving field
Author: Gautam Patel Publisher: Elsevier ISBN: 0443223254 Category : Technology & Engineering Languages : en Pages : 660
Book Description
Modern advances in organic synthesis require compouds having attractive properties with high percentage of yield. Spirooxindole examines the current state of the art, recent progress and new challenges associated with the development of spirooxindole derivatives for various medicinal applications. Owing to their exceptional properties, these compounds can be used in vaious fields, including chemical and pharma industries, and in clinical research. This book has chapters written by experts in several different areas. It serves as a useful reference book for scientists, industrial practitioners, graduate students, and other professionals in the field of hetrocyclic chemistry, medicinal chemistry, organic synthesis clinical research and chemical sciences.The growing interest among the academics and industrial researchers in the field of organic chemistry and medicinal chemistry is the driving force for the presentation of this edited book. Consolidates information on each aspect of this novel compound and its applications in various fields, covering the entire spectrum of up-to-date literature citations, current market, and patents Provides a comprehensive, in-depth description of spirooxindole derivatives as well as multipurpose scaffolds Highlights green synthesis and nanocatalysis Describes in-depth various medicinal applications Covers both synthesis and applications
Author: Kazuaki Ishihara Publisher: John Wiley & Sons ISBN: 3527348298 Category : Technology & Engineering Languages : en Pages : 452
Book Description
Iodine Catalysis in Organic Synthesis The first book of its kind to highlight iodine as a sustainable alternative to conventional transition metal catalysis Iodine Catalysis in Organic Synthesis provides detailed coverage of recent advances in iodine chemistry and catalysis, focusing on the utilization of various iodine-containing compounds as oxidative catalysts. Featuring contributions by an international panel of leading research chemists, this authoritative volume explores the development of environmentally benign organic reactions and summarizes catalytic transformations of molecular iodine and iodine compounds such as hypervalent organoiodine and inorganic iodine salts. Readers are first introduced to the history of iodine chemistry, the conceptual background of homogeneous catalysis, and the benefits of iodine catalysis in comparison with transition metals. Next, chapters organized by reaction type examine enantioselective transformations, catalytic reactions involving iodine, catalyst states, oxidation in iodine and iodine catalyses, and catalytic reactions based on halogen bonding. Practical case studies and real-world examples of different applications in organic synthesis and industry are incorporated throughout the text. An invaluable guide for synthetic chemists in both academic and industrial laboratories, Iodine Catalysis in Organic Synthesis: Provides a thorough overview of typical iodine-catalyzed reactions, catalyst systems, structures, and reactivity Explores promising industrial applications of iodine-based reagents for organic synthesis Highlights the advantages iodine catalysis has over classical metal-catalyzed reactions Discusses sustainable and eco-friendly methods in hypervalent iodine chemistry Edited by two world authorities on the catalytic applications of organoiodine compounds, Iodine Catalysis in Organic Synthesis is required reading for catalytic, organic, and organometallic chemists, medicinal and pharmaceutical chemists, industrial chemists, and academic researchers and advanced students in relevant fields.
Author: Martin Youngjin Pettersson
Author: Martin Youngjin Pettersson
Author: Zhihong Zhang
Author: John ApSimon
Author: John ApSimon
Author: E.J. Corey
Author: Navjeet Kaur
Author: N. H. Andersen
Author: Gautam Patel
Author: 
Author: Kazuaki Ishihara