Chemistry of Natural Products: A Unified Approach

N R Krishnaswamy

ISBN: 9788173716775 | Year: 2010 | Paperback | Pages: 432 | Language : English

Book Size: 180 x 240 mm | Territorial Rights: World

Price: 1075.00

Chemistry of Natural Products, A Unified Approach, provides a planned account of the common features structural and stereochemical of naturally occurring organic compounds). This is the only approach to bring about effective understanding of their chemistry. A variety of examples have been given to illustrate varied aspects so that the range of structure and behaviour exhibited by these compounds is retained within the set framework. The increasing application of physical (spectroscopic) methods like IR, NMR, CD, ORD, MS, High Resolution Mass Spectroscopy—using which, structural determinations are often done with very small or even microscopic quantities of the substance—is emphasised, without undermining the importance of ‘classical’ chemical methods. The section on problem solving helps to develop an analytical and critical evaluation of the data.

The Second Edition reflects the significant and important developments that have taken place since the publication of the first edition, particularly with regard to the biological aspects of natural products.


  • Unified approach: Discusses all classes of compounds
  • Unique approach: Discusses common structural and stereochemical features of naturally occurring organic compounds
  • Page extent increased by 200 pages
  • New chapter: Introduction
  • Revised Introduction for all chapters
  • Examples: About 100 examples across the book and 6 new per chapter
  • Correlation with spectral data
  • Problems: 5 additional problems

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.

1 Introduction
1.1 The terpenes
1.2 The alkaloids
1.3 Flavonoids and related compounds
1.4 Xanthones
1.5 Other oxygen heterocyclic compounds
1.6 Quinonoid compounds
1.7 Lichen metabolites
1.8 Concluding remarks
2 Structure
2.1 Introduction: A survey of the methods used for determination of structures
2.2 Strychnine: A hard nut to crack!
2.3 Nepitrin and pedaliin: A case of mistaken identity!
2.4 Colchicine: Structure from ’armchair’ research!
2.5 Longifolene: A molecular acrobat!
2.6 β-amyrin: A ’straight’ molecule
2.7 Wedelolactone: The fi rst of the coumestans
2.8 Protoaphin-fb : An insect pigment
2.9 Tylophorine: Another ’straight’ molecule with a kink or two!
2.10 Heliangine: An anti-auxin
2.11 Delphisine: Confi rmation of a structure by NMR spectra
2.12 Tubocurarine: The sting in the arrow
2.13 Sclerophytins A and B: Cytotoxic diterpenes from marine coral
2.14 Mangiferin: Parent of the Indian yellow
2.15 Conessine: A pseudo alkaloid
3 Stereochemistry
3.1 Introduction
3.2 Absolute stereochemistry of morphine
3.3 Quinine and related alkaloids
3.4 Emetine
3.5 Enhydrin
3.6 Conformations of naturally occurring germacranolides
3.7 Stereochemistry of rotenoids
3.8 Lactone fusion in sesquiterpene lactones
3.9 Stereochemistry of abietic acid
3.10 Catechins
3.11 Sphingosine
3.12 Stereochemistry of menthol
3.13 Stereochemistry of the kamahines
3.14 Absolute confi guration of benzyl isoquinoline alkaloids
3.15 Stereochemistry of some indole alkaloids
4 Reactions and Rearrangements
4.1 Introduction
4.2 Rearrangement reactions of morphine
4.3 Smaller and more agile molecular acrobats
4.4 The Wesley–Moser rearrangement
4.5 Some interesting reactions of reserpine
4.6 Molecular yoga: Reactions of papaverine
4.7 Two examples of transannular reactions
4.8 The epoxide as a medium of articulation
4.9 Capillarisin: An example of SN2 displacement
4.10 The reverse of a transannular cyclisation
4.11 The epoxide group as a ’handle’ for conversion
4.12 Reactions of linalool
4.13 The Nametkin rearrangement
4.14 Reactions of caryophyllene
4.15 Santonin to desmotroposantonin: An example of dienone–phenol rearrangement
5 Synthesis
5.1 Introduction
5.2 Synthesis of polyoxygenated fl avones with uncommon oxygenation patterns
5.3 Two contrasting syntheses of anthracyclinones
5.4 An approach to quassinoid synthesis
5.5 Synthesis of a semiochemical
5.6 A synthesis of polygodial
5.7 Balsamiferone and gravelliferone
5.8 Gyrinal: Defensive secretion of an insect
5.9 Synthesis of an unusual methylthiophenanthrene diol
5.10 A synthesis of (−) khusimone
5.11 Synthesis of a chiral marine natural product
5.12 A biomimetic synthesis of morphine
5.13 Synthesis of ergocristine
5.14 A stereoselective synthesis of reserpine
5.15 Synthesis of a paraconic acid
6 Biosynthesis
6.1 Introduction
6.2 Biosynthesis of some benzylisoquinoline alkaloids
6.3 Reticuline to morphine
6.4 From phenylalanine to colchicine
6.5 Tryptophan to quinine
6.6 Biosynthesis of some indole alkaloids
6.7 Biosynthesis of ergot alkaloids
6.8 Evolution of the monoterpenes
6.9 From mevalonic acid to the sesquiterpenes
6.10 Biosynthesis of some diterpenes
6.11 A brief note on the biosynthesis of ophiobolins
6.12 Geranyl pyrophosphate to lanosterol and the triterpenes
6.13 Non-nitrogenous secondary metabolites from shikimic acid: Flavonoids and related polyphenols
6.14 Biosynthesis and transformations of isofl avones
6.15 Biosynthesis of anthraquinones
7 Biological Significance of Secondary Metabolites
7.1 Introduction
7.2 Semiochemicals: An overview
7.3 Insect pheromones
7.4 Plant–insect interactions
7.5 Plant–vertebrate interactions
7.6 Plant–plant interactions
7.7 Plant–microbe interactions
7.8 Phytoalexins
7.9 Insect–animal interactions
7.10 Defensive secretions of insects
8 Problems
Index
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