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.
Introduction Th e terpenes Th e 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! beta-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 (ae') 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