Chemistry of Natural Products: A Unified Approach, Second Edition, 2nd Edition (Hardback) book cover

Chemistry of Natural Products

A Unified Approach, Second Edition, 2nd Edition

By N R Krishnaswamy

CRC Press

432 pages

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Hardback: 9781439849651
pub: 2010-09-24
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Description

The second edition of a bestseller, this book discusses the common structural and stereochemical features of naturally occurring organic compounds. It includes a variety of examples to illustrate varied aspects so that the range of structure and behavior exhibited by these compounds is retained within the set framework. The author explores the increasing application of physical (spectroscopic) methods like IR, NMR, CD, ORD, MS, and High Resolution Mass Spectroscopy without undermining the importance of classical chemical methods. The section on problem solving helps to develop an analytical and critical evaluation of the data.

Table of Contents

Introduction

The terpenes

The alkaloids

Flavonoids and related compounds

Xanthones

Other oxygen heterocyclic compounds

Quinonoid compounds

Lichen metabolites

Concluding remarks

Structure

Introduction: A survey of the methods used for determination of structures

Strychnine: A hard nut to crack!

Nepitrin and pedaliin: A case of mistaken identity!

Colchicine: Structure from ‘armchair’ research!

Longifolene: A molecular acrobat!

β-amyrin: A ‘straight’ molecule

Wedelolactone: Th e first of the coumestans

Protoaphin-fb : An insect pigment

Tylophorine: Another ‘straight’ molecule with a kink or two!

Heliangine: An anti-auxin

Delphisine: Confi rmation of a structure by NMR spectra

Tubocurarine: Th e sting in the arrow

Sclerophytins A and B: Cytotoxic diterpenes from marine coral

Mangiferin: Parent of the Indian yellow

Conessine: A pseudo alkaloid

Stereochemistry

Introduction

Absolute stereochemistry of morphine

Quinine and related alkaloids

Emetine

Enhydrin

Conformations of naturally occurring germacranolides

Stereochemistry of rotenoids

Lactone fusion in sesquiterpene lactones

Stereochemistry of abietic acid

Catechins

Sphingosine

Stereochemistry of menthol

Stereochemistry of the kamahines

Absolute confi guration of benzyl isoquinoline alkaloids

Stereochemistry of some indole alkaloids

Reactions and Rearrangements

Introduction

Rearrangement reactions of morphine

Smaller and more agile molecular acrobats

The Wesley–Moser rearrangement

Some interesting reactions of reserpine

Molecular yoga: Reactions of papaverine

Two examples of transannular reactions

The epoxide as a medium of articulation

Capillarisin: An example of SN2 displacement

The reverse of a transannular cyclisation

The epoxide group as a ‘handle’ for conversion

Reactions of linalool

The Nametkin rearrangement

Reactions of caryophyllene

Santonin to desmotroposantonin: An example of dienone–phenol rearrangement

Synthesis

Introduction

Synthesis of polyoxygenated fl avones with uncommon oxygenation patterns

Two contrasting syntheses of anthracyclinones

An approach to quassinoid synthesis

Synthesis of a semiochemical

A synthesis of polygodial

Balsamiferone and gravelliferone

Gyrinal: Defensive secretion of an insect

Synthesis of an unusual methylthiophenanthrene diol

A synthesis of (−) khusimone

Synthesis of a chiral marine natural product

A biomimetic synthesis of morphine

Synthesis of ergocristine

A stereoselective synthesis of reserpine

Synthesis of a paraconic acid

Biosynthesis

Introduction

Biosynthesis of some benzylisoquinoline alkaloids

Reticuline to morphine

From phenylalanine to colchicine

Tryptophan to quinine

Biosynthesis of some indole alkaloids

Biosynthesis of ergot alkaloids

Evolution of the monoterpenes

From mevalonic acid to the sesquiterpenes

Biosynthesis of some diterpenes

A brief note on the biosynthesis of ophiobolins

Geranyl pyrophosphate to lanosterol and the triterpenes

Non-nitrogenous secondary metabolites from shikimic acid: Flavonoids and related polyphenols

Biosynthesis and transformations of isofl avones

Biosynthesis of anthraquinones

Biological Significance of Secondary Metabolites

Introduction

Semiochemicals: An overview

Insect pheromones

Plant–insect interactions

Plant–vertebrate interactions

Plant–plant interactions

Plant–microbe interactions

Phytoalexins

Insect–animal interactions

Defensive secretions of insects

Problems

Index

About the Author

Dr N R Krishnaswamy has over 30 years of teaching experience in institutions such as the All India Institute of Medical Sciences, New Delhi, University of Delhi, Bangalore University, Calicut University and Sri Sathya Sai Institute of Higher Learning, where he was Professor and Head, Department of Chemistry.

Subject Categories

BISAC Subject Codes/Headings:
MED071000
MEDICAL / Pharmacology
SCI013000
SCIENCE / Chemistry / General