Strategies and Tactics in Organic Synthesis - 1st Edition - ISBN: 9780124171855, 9780124171916

Strategies and Tactics in Organic Synthesis, Volume 10

1st Edition

Editors: Michael Harmata
eBook ISBN: 9780124171916
Hardcover ISBN: 9780124171855
Imprint: Academic Press
Published Date: 18th July 2014
Page Count: 320
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Table of Contents

  • Dedication
  • Preface
  • Chapter 1: Substrate-Directed Heck–Matsuda Arylations: From Curiosity to a Valuable Synthetic Tool
    • Abstract
    • 1 Introduction and Overview
    • 2 Substrate-Directed Heck–Matsuda Reaction
    • 3 Development and Synthetic Applications of the Substrate-Directed Heck–Matsuda Reaction
    • 4 Conclusion
    • Acknowledgments
  • Chapter 2: (−)-Berkelic Acid: Lessons Learned From Our Investigations on a Scalable Total Synthesis
    • Abstract
    • 1 Introduction: Isolation and Interest on Berkelic Acid
    • 2 Structural Assignation and Previous Total Syntheses of (−)-Berkelic Acid
    • 3 Our Approach to Berkelic Acid from Research on New Methodology: Model Studies
    • 4 Retrosynthetic Analysis
    • 5 Our Synthesis of (−)-Berkelic Acid
    • 6 Conclusions
    • Acknowledgments
  • Chapter 3: The Mysterious Case of the Kingianins
    • Abstract
    • 1 Introduction—What's Going on Here?
    • 2 Analysis of the Problem—Regio- and Stereochemical Issues
    • 3 Preliminaries: Tests of the RCDA Approach with Model Compounds
    • 4 Selecting a Strategy for the Total Synthesis of Kingianin A
    • 5 Getting Started: Synthesis of a Pre-Kingianin A Equivalent
    • 6 Pursuit of the Intramolecular RCDA Approach
    • 7 Synthesis of Kingianin A
    • 8 “Go Fish”—Pursuit of the Intermolecular RCDA Approach
    • 9 Formal Synthesis of Kingianin A and Synthesis of Kingianins D, F, H, and J
    • 10 NCI 60 Test Results for Kingianins A (NSC#D-768505/1) and H (NSC#D-768506/1)
    • 11 Reconsidering the Biosynthesis
    • 12 Conclusions
    • Acknowledgments
  • Chapter 4: Total Synthesis of Chinensiolide B: An Exercise in Functional Group Selectivity with the Help of a Fortuitous Side Product and a Good Nose
    • Abstract
    • 1 Introduction
    • 2 Model Studies and Retrosynthetic Analysis
    • 3 Design and Synthesis of the Key Allylboronate
    • 4 Synthesis of the Cyclopentyl Aldehyde Substrate
    • 5 Critical Moment—The Key Aldehyde Allylboration Step
    • 6 Seven-Membered Ring Generation
    • 7 Installation of the Tertiary Alcohol and Final Steps
    • 8 Conclusions
    • Acknowledgments
  • Chapter 5: Syntheses of the Bisindole Alkaloids of the Genera Borreria and Flindersia
    • Abstract
    • 1 Introduction and Background
    • 2 Biosynthetic Proposals
    • 3 Synthetic Approaches to the Flinderoles
    • 4 Biomimetic Synthesis of the Flinderoles and Borreverines in Three Steps
    • 5 Optical Activity
    • 6 Conclusion
  • Chapter 6: Synthesis of (±)-Amathaspiramide F: Stereochemical Switch of a [2,3]-Stevens Rearrangement
    • Abstract
    • 1 Introduction
    • 2 Amathaspiramide Alkaloids
    • 3 Previous Syntheses of Amathaspiramides
    • 4 Retrosynthetic Analysis of Amathaspiramides
    • 5 Initial Route to Amathaspiramide A
    • 6 Role of ortho-Substitution of Aromatic Carbonates
    • 7 Formal Synthesis of Amathaspiramide F
    • 8 Concluding Remarks
    • Acknowledgments
  • Chapter 7: Oxabicyclic Building Blocks as Key Intermediates in the Synthesis of the Natural Products (−)-Platensimycin and (+)-Frondosin A
    • Abstract
    • 1 Introduction
    • 2 Formal Total Synthesis of (−)-Platensimycin
    • 3 Asymmetric Total Synthesis of (+)-Frondosin A
    • 4 Conclusion
  • Chapter 8: Structure Inspires a New Method That Delivers the Synthesis of Natural Products and Analogs in the Pederin Family
    • Abstract
    • 1 Introduction
    • 2 Total Synthesis of Theopederin D
    • 3 Psymberin
    • 4 N-Acylaminals from Nitrile Hydrozirconation
    • 5 Total Synthesis of Pederin
    • 6 Total Synthesis of Psymberin
    • 7 Analog Synthesis
    • 8 Biological Studies
    • 9 Conclusions
    • Acknowledgments
  • Chapter 9: Gliocladin C: The Development and Application of a Pyrroloindoline–Indole Radical Coupling Reaction
    • Abstract
    • 1 Introduction
    • 2 Retrosynthetic Strategies and Model System Studies
    • 3 Synthesis of the C3—C3′ Bisindole Skeleton
    • 4 Backbone Oxidation and TKP Formation Studies
    • 5 Conclusion
    • Acknowledgments
  • Chapter 10: Studies in the Synthesis of Biaryl Natural Products: The 6,6′-Binaphthopyranones
    • Abstract
    • 1 Introduction
    • 2 Axial Chirality and Biaryl Natural Products
    • 3 Strategies in the Assembly of Biaryl Natural Products: Instructive Examples that Shaped Synthetic Planning for Viriditoxin
    • 4 Retrosynthetic Analysis of Viriditoxin and Related Natural Products
    • 5 Assembly of Viriditoxin, Pigmentosin A, Talaroderxine A, Talaroderxine B
    • 6 Biological Activity of the 6,6′-Binaphthopyranones
    • 7 Conclusion
    • Acknowledgments
  • Chapter 11: Sleepless Nights: The Total Synthesis of the Anticancer Australian Rainforest Polyketide EBC-23
    • Abstract
    • 1 Introduction
    • 2 Structure Elucidation
    • 3 Retrosynthetic Plan
    • 4 Starting the Total Synthesis
    • 5 Understanding Acyl Anion Equivalents
    • 6 Tietze–Smith Linchpin Reaction
    • 7 Refining the Synthetic Campaign
    • 8 Completing the Total Synthesis
    • 9 Biomimetic Attempts
    • 10 Yamamoto Synthesis
    • 11 Conclusion
    • Acknowledgments
  • Chapter 12: Total Synthesis of the Crinipellins
    • Abstract
    • 1 Introduction and Background
    • 2 The First Approach
    • 3 The Second Approach: Formal Total Synthesis of Crinipellin B
    • 4 Asymmetric Total Synthesis of Crinipellins
  • Index

Description

A classic in the area of organic synthesis, Strategies and Tactics in Organic Synthesis provides a forum for investigators to discuss their approach to the science and art of organic synthesis. Rather than a simple presentation of data or a secondhand analysis, we are given stories that vividly demonstrate the power of the human endeavor known as organic synthesis and the creativity and tenacity of its practitioners. Firsthand accounts of each project tell of the excitement of conception, the frustration of failure and the joy experienced when either rational thought or good fortune gives rise to the successful completion of a project. This book series shows how synthesis is really done, and we are educated, challenged and inspired by these accounts, which portray the idea that triumphs do not come without challenges. We also learn that we can meet challenges to further advance the science and art of organic synthesis, driving it forward to meet the demands of society, in discovering new reactions, creating new designs and building molecules with atom and step economies that provide solutions through function to create a better world.

Key Features

  • Presents state-of-the-art developments in organic synthesis
  • Provides insight and offers new perspective to problem-solving
  • Written by leading experts in the field

Readership

Organic chemists; academic libraries, chemical and pharmaceutical companies


Details

No. of pages:
320
Language:
English
Copyright:
© Academic Press 2014
Published:
Imprint:
Academic Press
eBook ISBN:
9780124171916
Hardcover ISBN:
9780124171855

About the Editors

Michael Harmata Editor

Professor Michael Harmata graduated from the University of Illinois-Chicago with honors and highest distinction in chemistry.

In 1980, he began graduate studies in chemistry at the University of Illinois-Champaign/Urbana where he was awarded a University Teaching Fellowship. He worked with Professor Scott E. Denmark on the invention of the carbanion-accelerated Claisen rearrangement. In his second year of study, he was awarded an Eastman Kodak Research Fellowship.

Upon graduation in 1985, he was awarded an NIH postdoctoral fellowship which he used to study with Professor Paul A. Wender at Stanford University, where he worked on the synthesis of the neocarzinostatin chromophore.

In 1986, Prof. Harmata began his independent career at the University of Missouri-Columbia. He became an Associate Professor in 1992 and a full professor in 1998. In 2000, he was named the Norman Rabjohn Distinguished Professor of Chemistry in recognition of his achievements in research and teaching. In 1998, he received a research fellowship from the Alexander von Humboldt Foundation and stayed for a year at the University of Göttingen where he was affiliated with the groups of Professors Reinhard Brückner and Lutz. F. Tietze. In 2000, he served as chair of the Gordon conference on Organic Reactions and Processes. In 2010, he was named the first Justus Liebig Professor of Chemistry at the Justus Liebig Üniversität in Giessen, Germany. In 2011, he was a JSPS fellow. He has been a visiting professor in Giessen and Strasbourg and has delivered over 180 invited lectures in the United States and Europe. He is a member of the American Chemical Society, Gesellschaft Deutscher Chemiker, International Society of Heterocyclic Chemistry, and the Alexander von Humboldt Association of America.

Affiliations and Expertise

University of Missouri, MO, USA