Indole Alkaloids

Spirooxindole

1st Edition - January 30, 2022
Authors: Maliha Uroos, Abdul Hameed, Sadia Naz, Muhammad Raza Shah
Language: English
Paperback ISBN:
9 7 8 - 0 - 3 2 3 - 9 1 6 7 4 - 5
eBook ISBN:
9 7 8 - 0 - 3 2 3 - 9 7 2 4 8 - 2

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… Read more

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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.

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

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

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 a 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. Professor Shah has authored six books and edited four 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.

Affiliations and expertise

Professor, International Center for Chemical and Biological Sciences, H.E.J. Research Institute of Chemistry University, Karachi, Pakistan