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.
1 Department of Chemistry, Faculty of Science, Alexandria University, Alexandria, Egypt.
2 Environmental Division, National Institute of Oceanography and Fisheries, Kayet Bay, Alexandria, Egypt.
1.1 Hydroxymethylpyrrolidines.
2-Hydroxymethyl-pyrrolidines.
Dihydro-2-hydroxymethylpyrrole (Nectrisine).
2,5-Dihydroxymethyl-pyrrolidines.
1.2 2-Carboxypyrrolidines.
Hydroxyprolines.
Bulgecins.
1.3 2-Aralkyl pyrrolidines.
Anisomycin.
Preussin.
1.4 2-Aryl pyrrolidines.
Codonopsinine and Codonopsine.
1.5 Miscellaneous.
Detoxins.
Gualamycin.
Lactacystin.
Chapter 2 Five Membered Heterocycles with two Heteroatoms.
2.1 Hydantocidin.
2.2 Bleomycin.
2.3 Calyculins.
2.4 Acivicin.
2.5 Bengazole.
Chapter 3 Six Membered Nitrogen Heterocycles.
3.1 Hydroxymethylpiperidines.
Nojirimycin.
Mannojirimycin.
Galactonojirimycin.
Fagomine.
Homojirimycins.
3.2 Miscellaneous substituted piperidines.
2,6-Disubstituted-3-hydroxypiperidines.
Hydroxylated pipicolic acid.
Sesbanimide.
Siastatin.
Meroquinene.
Pyridyl of pyridomycin.
Chapter 4 Seven Membered Nitrogen Heterocycles.
4.1 Bengamides.
4.2 Liposidomycins.
Chapter 5 Fused Nitrogen Heterocycles.
5.1 3:5-Fused Heterocycles.
Azinomycins.
5.2 4:5-Fused Heterocycles.
b-Lactams.
5.3 5:5-Fused Heterocycles.
Polyhydroxypyrrolizidines.
Trehazolin.
Allosamidin.
Biotin.
5.4 5:6-Fused Heterocycles.
Hydroxylated indolizidines.
Castanospermine.
Swainsonine.
Lentiginosine.
Slaframine.
Miscellaneous.
Kifunensine.
Nagastatin.
Calystegines.
Mesembrine.
Streptolidine.
55 6:6-Fused Heterocycles.
Hydroxylated Quinuclidines.
Biopterins.
Isoquinolines.
Calycotomine.
Decumbenosine.
Laudanosine and glaucine.
Chapter 6 Multi-fused heterocycles.
6.1 Indoloquinolizidines.
Xylopinine.
Antirhine.
Allo-Yohimbane.
Ajmalicine.
6.2 Indolocarbazole Alkaloids.
6.3 Phenanthridone alkaloids.
6.4 Ecteinascidins
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