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E-grāmata: Progress in the Chemistry of Organic Natural Products 118

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This volume consists of four chapters that cover a structurally diverse range of naturally occurring compounds. Chapter 1 delves into the chemistry of pyrogallols and their oxidized products, the hydroxy-o-quinones, including their role in cycloaddition reactions in the chemical synthesis of several fungal metabolites. Chapter 2 provides an in-depth description of the constituents of agarwood essential oil and smoke samples that are used in the perfumery industry, with an emphasis on the sesquiterpenoid and chromones constituents so far known. Chapter 3 discusses the defensive chemical ecology of two North American newt species that both produce tetrodotoxin, a well-known neurotoxin that causes paralysis and death in metazoans by disrupting electrical signals in the nerves and muscles. Chapter 4 discusses the limonoids and triterpenoids from the genus Walsura of the plant family Meliaceae, of which a number of species are utilized in several southeastern Asian countries in systems of folk medicine.

Complex Natural Products Derived from Pyrogallols
Alexander J. E. Novak
Dirk Trauner Contents
1 Introduction
2(1)
2 Oxidation of Pyrogallols and Their Reactivity
2(11)
2.1 A [ 5+2] Cycloaddition in the Purpurogallin Cascade
3(5)
2.2 The Formation of the Perkin Dimer
8(2)
2.3 The Hetero-Diels-Alder Dimerization of Pyrogallols
10(1)
2.4 Guidelines to Substrate Dependent-Reactivity Trends
10(3)
3 Complex Pyrogallol-Derived Natural Products from Epicoccum spp
13(9)
3.1 Biomimetic Synthesis of the Calcineurin Phosphatase Inhibitor Dibefurin, a Perkin-Type Dimer
13(3)
3.2 Biomimetic Synthesis of Epicolactone by a Modified Purpurogallin Cascade
16(4)
3.3 Beetleane A and Epicoane A--Two Perkin-Type Dimer-Derived Natural Products
20(2)
4 [ 5+2] Cycloadditions in the Synthesis of the Merocytochalasans
22(16)
4.1 Overview of and Biosynthesis Hypothesis for the Merocytochalasans
23(4)
4.2 Syntheses of the Asperchalasines
27(6)
4.3 Synthesis of the Aspergilasines, Amichalasines, Asperflavipines, and Epicochalasines
33(5)
5 Preuisolactone A--Another Racemic Fungal Natural Product
38(4)
References 42