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Design and Strategy in Organic Synthesis: From the Chiron Approach to Catalysis

ISBN: 978-3-527-31964-0
822 pages
September 2013
Design and Strategy in Organic Synthesis: From the Chiron Approach to Catalysis (3527319646) cover image

Description

This long-awaited graduate level book, written by one of the world's leading organic chemists in collaboration with two of his former and present coworkers, adopts a refreshingly unique approach to synthesis planning and execution. Following an introductory look at the concept of synthesis, the authors discuss the Why, What, and How of organic synthesis as they apply to natural products. Although emphasis is on the Chiron Approach utilizing amino-acids, carbohydrates, hydroxy acids, terpenes, lactones and other naturally occurring small molecules as starting materials, catalytic asymmetric methods are also included as a corollary whenever relevant.

A must-have source of first class information for everyone working in organic synthesis, be it in academia or industry.

With a foreword by Larry E. Overman and David W. C. MacMillan
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Table of Contents

PREFACE

THE CONCEPT OF SYNTHESIS
Organic Synthesis as a Central Science
Organic Chemistry and the Public
The 'Small Molecules' of life
Nature's Rules
Organic Synthesis as a Mental and Visual Science
Art, Architecture, and Synthesis
Simplification of Complexity
Seeing Through the Mind's Eye
Beauty is in the Eye of the Beholder

THE 'WHY' OF SYNTHESIS
Nature the Provider, Healer, and Enticer
The Supply Problem
From Bench to Market
Thank you Nature!
Chasing Bugs with a Purpose
Structure-based Organic Synthesis
Almost There . . . or Just Arrived
The Futility of it All
Synthesis as a Seeker of the Truth
Nature as the Ultimate Synthesizer
A Brave New Chemical World
Exploring New Synthetic Methods

THE 'WHAT' OF SYNTHESIS
Periods, Trends, and Incentives
A Century of Synthesis
We the 'Synthesis People'
Complex and Therapeutic too!
Peptidomimetics and Unnatural Compounds
Diversity Through Complexity

THE 'HOW' OF SYNTHESIS
The Visual Dialogue
The Psychobiology of Synthesis Planning
The Agony and Ecstasy of Synthesis
Rembrandt Meets Woodward
The Post Woodwardian Era
Catalysis and Chirality in Total Synthesis

SOURCES OF ENANTIOPURE COMPOUNDS
Optical Resolution
Chemical Kinetic Resolution (KR)
Cell-free Enzyme-mediated Enantiopure Compounds
Cell-free Chemoenzymatic Methods
Metal-catalyzed Dynamic Kinetic Resolution (DKR)
Biocatalytic Methods for Enantiopure Compounds
Applications of Enzymatic and Chemoenzymatic Methods
Chemical Asymmetric Synthesis of Enantiopure Compounds
Enantiopure Compounds from Nature

THE CHIRON APPROACH
Living Through a Total Synthesis
Principles of the Chiron Approach
Anatomy of a Synthesis

NATURE'S CHIRONS
Alpha-Amino Acids
Carbohydrates
Alpha-Hydroxy Acids
Terpenes
Cyclitols

FROM TARGET MOLECULE TO CHIRON
Where's Waldo?
Apparent Chirons
Partially Hidden Chirons
Hidden Chirons
Chirons as 'Sacrificial Lambs'
Locating alpha-Amino Acid-type Substructures
Locating Carbohydrate-type Substructures
Locating Hydroxy Acid-type Substructures
Locating Terpene-type Substructures
Locating Carbocyclic-type Substructures
Locating Chirons Derived from Lactones

APPLICATIONS OF THE CHIRON APPROACH
Category I Target Molecules
Category II Target Molecules
Category III Target Molecules
Prelude to Total Synthesis of Category I Molecules

TOTAL SYNTHESIS FROM ALPHA-AMINO ACID PRECURSORS
Actinobolin
Aspochalasin B
Cephalotaxine 329
Alpha-Kainic Acid (W. Oppolzer)
Alpha-Kainic Acid (P. T. Gallagher)
Croomine
Biotin
Salinosporamide A
Thienamycin
FR901483
Tuberostemonine
Phyllanthine
Oscillarin
ent-Cyclizidine
Pactamycin
Miscellanea

TOTAL SYNTHESIS FROM CARBOHYDRATE PRECURSORS
Ajmalicine
ent-Actinobolin
Trehazolin and Trehazolamine
Fomannosin
9a-Desmethoxy Mitomycin A
Saxitoxin and ß-Saxitoxinol
ent-Decarbamoyl Saxitoxin
Zaragozic acid A
Hemibrevetoxin B
Carbohydrates in Synthesis and in Biology
Miscellanea

TOTAL SYNTHESIS FROM HYDROXY ACIDS
Griseoviridin
Halicholactone
Brasilenyne
Octalactin A
(3Z)-Dactomelyne
UCS1025A
Jerangolid A
Miscellanea

TOTAL SYNTHESIS FROM TERPENES
Picrotoxinin
Eucannabinolide
Trilobolide and Thapsivillosin F
Briarellin E and F
Samaderine Y
Ambiguine H and Hapalindole U
Platensimycin
Phomactin A
Pinnaic Acid
Fusicoauritone
Miscellanea

TOTAL SYNTHESIS FROM CARBOCYCLIC PRECURSORS
Punctatin A
Acanthoic Acid
Stachybocin Spirolactam
Scabronine G
Chapecoderin A
Dragmacidin F
Reserpine
Fawcettimine
Tamiflu
Miscellanea

TOTAL SYNTHESIS WITH LACTONES AS PRECURSORS
Megaphone
Dihydromevinolin
Mannostatin A
Furaquinocin C
Miscellanea

SINGLE TARGET MOLECULE-ORIENTED SYNTHESIS
Synchronicity
Joining Forces
Back-to-back Publishing
Same Year Publications
Single Target Molecules with Special Relevance
Quinine
Lactacystin
Taxol

MAN, MACHINE, AND VISUAL IMAGERY IN SYNTHESIS PLANNING
The LHASA Program
SYNGEN
WODCA
The CHIRON Program
Computer-aided synthesis planning

THE ESSENCE OF SYNTHESIS -
A RETROSPECTIVE
Lest we Forget
The Corey and Stork Schools
The Visual Dialogue with Molecules
Total Synthesis: From whence we came. . .
In Pursuit of the 'Ideal Synthesis'
For the Love of Synthesis (Synthephilia)
Organic Synthesis: To where we are going
Synthesis at the Service of Humankind
From the Chiron Approach to Catalysis
A Salute to the Vanguards of Synthesis
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Author Information

Stephen Hanessian holds the Isis Pharmaceutical Research Chair at the University of Montreal and is also on the faculty of the Departments of Chemistry, Pharmaceutical Sciences and Pharmacology at the University of California, Irvine. He has received numerous awards and distinctions, the latest being the 2012 Ernest Guenther Award in the Chemistry of Natural Products from the American Chemical Society, and the IUPAC-Richter-Preis in Medicinal Chemistry.

Simon Giroux was born and raised in Montreal, Canada. He received his PhD in 2006 with Prof. Stephen Hanessian and subsequently spent 2 years in the laboratory of Prof. E. J. Corey at Harvard University, as an NSERC postdoctoral fellow. He is currently working as a medicinal chemist at Vertex Pharmaceuticals in Cambridge, Massachusetts.

Bradley L. Merner is a native of St. John's, Newfoundland, Canada. He completed is PhD degree under the direction of Prof. Graham J. Bodwell at Memorial University in 2010, and then moved to the University of Montreal as postdoctoral research associate in the laboratories of Prof. Stephen Hanessian. In the fall of 2013 he will join the Department of Chemistry and Biochemistry at Auburn University as an Assistant Professor.
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Related Websites / Extra

2012 IUPAC-Richter Prize Professor Stephen Hanessian has been awarded the 2012 IUPAC-Richter Prize. Read the announcement...
2012 Ernest Guenther Award Professor Stephen Hanessian has won the 2012 Ernest Guenther Award in Natural Products Chemistry from the American Chemical Society (ACS). Find out more...
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