Synthesis of Naturally Occurring Nitrogen Heterocycles from Carbohydrates

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.

Carbohydrates are widely distributed in nature and widelyavailable, and so are considered as a promising feedstock for thepreparation of many organic chemical compounds. They areparticularly useful in the preparation of nitrogen heterocyclesbecause of their related structural characteristics and easyavailability.Synthesis of Naturally Occurring Nitrogen Heterocycles fromCarbohydrates will review the recent literature dealing withuse of carbohydrates as raw materials in the synthesis of thesematerials. The text contains six chapters arranged according to thecomplexity of the heterocyclic compounds discussed, ranging fromfive to seven membered rings and from single to multiple fusedrings. The book provides a detailed discussion of the varioussynthetic approaches to these compounds, using carbohydratestarting materials, and does not merely reference syntheticmethodology but attempts to give as much detail as possible on theactual experimental conditions used, in such a way that the chemistcan use the information directly to design a multi-step synthesis.It discusses the different approaches to the synthesis of a widerange of naturally occurring nitrogen heterocycles in a format thatenables the reader to make comparisons and decisions on whether touse a certain procedure, to modify it, or to devise a new syntheticmethodology.

Chapter 1 Five Membered Nitrogen Heterocycles.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 twoHeteroatoms.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