Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates

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Format: eBook
Pub. Date: 2008-04-01
Publisher(s): Wiley-Blackwell
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Summary

Carbohydrates are widely distributed in nature and widely available, and so are considered as a promising feedstock for the preparation of many organic chemical compounds. They are particularly useful in the preparation of nitrogen heterocycles because of their related structural characteristics and easy availability.Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates will review the recent literature dealing with use of carbohydrates as raw materials in the synthesis of these materials. The text contains six chapters arranged according to the complexity of the heterocyclic compounds discussed, ranging from five to seven membered rings and from single to multiple fused rings. The book provides a detailed discussion of the various synthetic approaches to these compounds, using carbohydrate starting materials, and does not merely reference synthetic methodology but attempts to give as much detail as possible on the actual experimental conditions used, in such a way that the chemist can use the information directly to design a multi-step synthesis. It discusses the different approaches to the synthesis of a wide range of naturally occurring nitrogen heterocycles in a format that enables the reader to make comparisons and decisions on whether to use a certain procedure, to modify it, or to devise a new synthetic methodology.

Table of Contents

Five Membered Nitrogen Heterocycles
Hydroxymethylpyrrolidines
2-Hydroxymethyl-pyrrolidines
Dihydro-2-hydroxymethylpyrrole (Nectrisine
2,5-Dihydroxymethyl-pyrrolidines
2-Carboxypyrrolidines
Hydroxyprolines
Bulgecins
2-Aralkyl pyrrolidines
Anisomycin
Preussin
2-Aryl pyrrolidines
Codonopsinine and Codonopsine
Miscellaneous
Detoxins
Gualamycin
Lactacystin
Five Membered Heterocycles with two Heteroatoms
Hydantocidin
Bleomycin
Calyculins
Acivicin
Bengazole
Six Membered Nitrogen Heterocycles
Hydroxymethylpiperidines
Nojirimycin
Mannojirimycin
Galactonojirimycin
Fagomine
Homojirimycins
Miscellaneous substituted piperidines
2,6-Disubstituted-3-hydroxypiperidines
Hydroxylated pipicolic acid
Sesbanimide
Siastatin
Meroquinene
Pyridyl of pyridomycin
Seven Membered Nitrogen Heterocycles
Bengamides
Liposidomycins
Fused Nitrogen Heterocycles
3:5-Fused Heterocycles
Azinomycins
4:5-Fused Heterocycles
b-Lactams
5:5-Fused Heterocycles
Polyhydroxypyrrolizidines
Trehazolin
Allosamidin
Biotin
5:6-Fused Heterocycles
Hydroxylated indolizidines
Castanospermine
Swainsonine
Lentiginosine
Slaframine
Miscellaneous
Kifunensine
Nagastatin
Calystegines
Mesembrine
Streptolidine
6:6-Fused Heterocycles
Hydroxylated Quinuclidines
Biopterins
Isoquinolines
Calycotomine
Decumbenosine
Laudanosine and glaucine
Multi-fused heterocycles
Indoloquinolizidines
Xylopinine
Antirhine
Allo-Yohimbane
Ajmalicine
Indolocarbazole Alkaloids
Phenanthridone alkaloids
Ecteinascidins
Table of Contents provided by Publisher. All Rights Reserved.

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