Indole Alkaloids
Spirooxindole
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Indole Alkaloids: Spirooxindole details the multistep synthesis of natural products using schematic diagrams, providing a quick-and-easy way to review and understand new and novel synthetic strategies to construct structural frameworks of natural products. As a volume in the Visual Guides to Natural Product Synthesis series, this book presents the schematic total syntheses of natural products containing a “spirooxindole” core structure. It covers spirooxindole molecules through visual diagrams, highlighting key steps involved in total, formal and semi-syntheses. Sections cover Brevianamide A and B, Citrinadin A and B, Coerulescine and Horsfiline, Elacomine and Isoelacomine, Gelsemine, Paraherquamide A and B, Rynchophylline, Isorynchophylline, and more. Visual layouts provide quick-and- easy access to developed synthetic routes towards the targeted spirooxindoles.
Key Features
- Outlines synthetic strategies for natural products bearing a spirooxindole core structure
- Includes schematic diagrams of multistep synthetic routes, highlighting key steps along the way
- Describes all routes for the formal synthesis, semi-synthesis and total synthesis of spirooxindole alkaloids
Readership
Researchers working in the area of organic synthesis and natural products, especially those who are involved in the development of new, efficient and novel methodologies for natural product synthesis
Table of Contents
- Cover image
- Title page
- Table of Contents
- Copyright
- List of figures
- List of schemes
- About the authors
- Preface
- Chapter 1. Introduction to spirooxindoles
- Abstract
- References
- Chapter 2. (−)-Affinisine
- Abstract
- 2.1 Fonseca’s first stereospecific total synthesis of (−)-affinisine (2014)
- 2.2 Improved total synthesis of (−)-affinisine (2017)
- References
- Chapter 3. (+)-Austamide
- Abstract
- 3.1 Hutchison’s total synthesis of (±)-austamide (1979)
- 3.2 Corey’s total synthesis of (+)-austamide (2000)
- References
- Chapter 4. Brevianamide A and B
- Abstract
- 4.1 Total syntheses of brevianamides A and B
- References
- Chapter 5. Citrinadin A and B
- Abstract
- 5.1 Syntheses of citrinadins A and B spirooxindole core
- 5.2 Total syntheses of citrinadins A and B
- References
- Chapter 6. Coerulescine and horsfiline
- Abstract
- 6.1 Total synthesis of coerulescine and horsfiline
- References
- Chapter 7. Elacomine and isoelacomine
- Abstract
- 7.1 Total syntheses of (±)-elacomine and (±)-isoelacomine
- References
- Chapter 8. Gelsemine
- Abstract
- 8.1 Total syntheses of gelsemine
- 8.2 Formal syntheses of gelsemine
- References
- Chapter 9. Paraherquamide A and B
- Abstract
- 9.1 Total syntheses of paraherquamides A and B
- 9.2 McWhorter’s formal synthesis of 6,7-dihydroxyoxindole; a subunit of paraherquamide A (1996)
- 9.3 Conversion of marcfortine A to paraherquamide A via paraherquamide B (1997)
- References
- Chapter 10. Rhynchophylline and isorhynchophylline
- Abstract
- 10.1 Total syntheses of (−)-rhynchophylline and (+)-isorhynchophylline
- 10.2 Semisyntheses of (−)-rhynchophylline and (+)-isorhynchophylline
- 10.3 Formal syntheses of (−)-rhynchophylline and (+)-isorhynchophylline
- References
- Chapter 11. Spirotryprostatin A
- Abstract
- 11.1 Total synthesis of spirotryprostatin A
- References
- Chapter 12. Spirotryprostatin B
- Abstract
- 12.1 Total syntheses of (−)-spirotryprostatin B
- References
- Chapter 13. Strychnofoline
- Abstract
- 13.1 Carreira’s first total synthesis of (±)-strychnofoline (2002)
- 13.2 Carreira’s racemic total synthesis of (±)-strychnofoline; highly convergent selective annulation reaction (2006)
- 13.3 Yu’s enantioselective synthesis of (−)-strychnofoline (2018)
- References
- List of abbreviations
- Index
Product details
- No. of pages: 240
- Language: English
- Copyright: © Elsevier 2022
- Published: January 30, 2022
- Imprint: Elsevier
- Paperback ISBN: 9780323916745
- eBook ISBN: 9780323972482
About the Authors
Maliha Uroos
Dr. Maliha Uroos completed her PhD in synthetic organic chemistry in 2012 from the University of Nottingham under HEC Faculty Development Scholarship. She was awarded EPSRC post-doctoral fellowship (2012-13) at the University of Nottingham, UK. She was appointed Lecturer at University of the Punjab in 2007 and currently working as Associate Professor (2020 to date) and Director, Centre for Research Ionic Liquid, School of Chemistry, University of the Punjab. Her main focus is synthetic organic chemistry and research interests include synthesis and applications of ionic liquids, synthesis of biologically active molecules, sustainable energy production and development of green processes for setting up bio-refinery from agricultural waste.
Abdul Hameed
Dr. Abdul Hameed Dr. Abdul Hameed completed his PhD in Organic Chemistry from The University of Nottingham, UK. He worked in the area of natural products synthesis. He was a post-doc fellow in Max-Planck Institut für Polymerforschung, Germany in synthetic division headed by Prof. Dr. Klaus Müllen. There he worked on the functionalization of adenylyl cyclsase inhibitors via chemical methods to conjugate them with monoclonal antibody to study their biological potential in Regulatory T cells (Treg). His current research interests are including the development of novel methodologies, their utilization in natural products synthesis, the synthesis heterocyclic compound compounds to evaluate their biological potential.
Affiliations and Expertise
Department of Chemistry, University of Sahiwal, Sahiwal 57000, Pakistan
Sadia Naz
Sadia Naz is currently a PhD student at Centre for Research Ionic Liquid, School of Chemistry, University of the Punjab (2018 to onwards) and is working as research assistant in HEC NRPU project with Dr. Maliha Uroos (2019 to onwards). She has publications in international journals and presented her work in various international and national conferences. Her research interests include synthetic organic chemistry, ionic liquids, conversion of agricultural waste materials into valuable platform chemicals.
Muhammad Raza Shah
Prof. Muhammad Raza Shah is a full professor at the International Center for Chemical and Biological Sciences, HEJ Research Institute of Chemistry, University of Karachi, Pakistan. He is also the Head of the Center for Bioequivalence Studies and Clinical Research. He is the recipient of several awards, including the Tamgha-i-Imtiaz Award from the President of Pakistan, the Salam Prize, the Professor Atta ur Rahman Gold Medal, and the Dr M Raziuddin Siddiqi Prize, by the Pakistan Academy of Sciences, for scientists under 40 years of age, in the field of chemistry. Prof. Shah has authored 3 books and edited 2 books, in addition to contributing over 350 peer-reviewed journal papers. One of his authored books was declared as best book of 2017 by the Government of Pakistan’s Higher Education Commission. He is an editor for the Journal of the Chemical Society of Pakistan, and has been a mentor of the Pakistani International Chemistry Olympiad team since 2009. Prof. Shah is a Fellow of both the International Union of Pure and Applied Chemistry and the Chemical Society of Pakistan, is a member of the National Nanotechnology Foresight Committee, constituted by the Pakistan Council for Science and Technology, and remains a member of the COMSTECH consultative working group of scientists from OIC countries, to prepare an agenda and action plan for the Ten-Year Plan of Action (TYPOA 2016-2025).
Affiliations and Expertise
Professor, International Center for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry University, Karachi, Pakistan